Substituted isophthalic acid diamides

ABSTRACT

Isophthalamides of the general formula (I) are described as herbicides.In this formula (I), X, Y and Z represent radicals such as hydrogen, alkyl and halogen. Q represents a heterocyclic ring such as tetrazolyl.

The invention relates to the technical field of herbicides, especially that of herbicides for selective control of broad-leaved weeds and weed grasses in useful plants.

WO 2012/028579 A1, WO 2012/126932 A1, WO2013/017559 A1 and WO 2017/144402 A1 describe, inter alia, herbicidally active isophthalamides which differ essentially by the nature of the substituents on the two amide functions.

The isophthalamides specifically disclosed therein always have a tertiary amide group. However, the isophthalamides known from these documents do not always have adequate herbicidal efficacy and/or compatibility with crop plants. It has been found that isophthalamides having a primary or secondary amide group have superior properties compared to the isophthalamides known from the prior art. The present invention thus provides isophthalamides of the formula (I) or salts thereof

in which the symbols and indices are defined as follows:

-   -   Q is Q¹, Q², Q³ or Q⁴

-   -   R¹ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl,     -   R² is (C₁-C₆)-alkyl,     -   R^(x) is (C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl or phenyl,     -   R^(y) is halogen, (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl,     -   R^(z) is hydrogen, (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl,     -   X is halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,         (C₃-C₆)-cycloalkyl, R¹O, R²(O)_(n)S or R¹O—(C₁-C₆)-alkyl or         R²S(O)_(n)—(C₁-C₆)-alkyl,     -   Y is halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O or         R²(O)_(n)S     -   Z is hydrogen,         -   one of the following groups, each of which is substituted by             s radicals from the group consisting of halogen, cyano,             R¹C(O), R¹OC(O), R¹O and R²(O)_(n)S: (C₁-C₆)-alkyl,             (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,             (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,             (C₂-C₆)-alkenyl-(C₁-C₆)-alkyl, (C₂-C₆)-alkynyl,             (C₂-C₆)-alkynyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,             R²S(O)n-(C₁-C₆)-alkyl, R¹C(O), R¹OC(O),             R¹C(O)—(C₁-C₆)-alkyl, R¹OC(O)—(C₁-C₆)-alkyl,             R¹NH—(C₁-C₆)-alkyl, R¹ ₂N—(C₁-C₆)-alkyl,             R¹NHC(O)—(C₁-C₆)-alkyl or R¹ ₂NC(O)—(C₁-C₆)-alkyl, or         -   one of the following groups, each substituted by s radicals             from the group consisting of halogen, (C₁-C₆)-alkyl,             halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,             R¹C(O) and R¹OC(O):         -   phenyl, benzyl, phenyl, benzyl, heterocyclyl or             heterocyclyl-(C₁-C₆)-alkyl,     -   n is 0, 1 or 2,     -   s is 0, 1, 2 or 3.

In the formula (I) and all the formulae which follow, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl, n-, iso-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Analogously, alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond may be in any position in each unsaturated radical. Cycloalkyl is a carbocyclic saturated ring system having three to six carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Halogen-substituted alkyl means straight-chain or branched alkyl groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms, e.g. C₁-C₂-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.

Halogen represents fluorine, chlorine, bromine or iodine.

A heterocyclic radical (heterocyclyl) is a 5- or 6-membered cyclic radical which, as well a carbon atoms, contains at least one heteroatom from the group of N, O, S, and which is saturated, unsaturated, partly saturated or heteroaromatic and may be unsubstituted or substituted, in which case the bonding site is localized on a ring atom. Example of heterocyclic radicals are 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetra-hydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridin-1- or 2- or 3- or 4-yl; 2,3-dihydropyridin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridin-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl, 2- or 3-oxolanyl (=2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (=2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-2- or 3-yl; tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl; 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazol-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyrazin-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-1- or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; 1,3-dioxolan-2- or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxan-2- or 4- or 5-yl; 4H-1,3-dioxin-2- or 4- or 5- or 6-yl; 1,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1,3-dithiin-2- or 4- or 5- or 6-yl; isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl; 1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-1,3-oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-oxazin-2- or 4- or 5- or 6-yl; morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; isothiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl.

Depending on the nature of the substituents and the manner in which they are attached, the compounds of the general formula (I) may be present as stereoisomers. If, for example, one or more asymmetrically substituted carbon atoms are present, there may be enantiomers and diastereomers. Stereoisomers likewise occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. It is likewise possible to selectively prepare stereoisomers by using stereoselective reactions with use of optically active starting materials and/or auxiliaries. The invention also relates to all the stereoisomers and mixtures thereof that are encompassed by the general formula (I) but are not defined specifically.

The compounds of formula (I) may form salts. Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine or pyridine, and the hydroxides, carbonates and hydrogencarbonates of ammonium, alkali metals or alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, especially alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR′R″R′″]⁺ in which R to R′″ are each independently an organic radical, especially alkyl, aryl, aralkyl or alkylaryl. Also useful are alkylsulfonium and alkylsulfoxonium salts, such as (C₁-C₄)-trialkylsulfonium and (C₁-C₄)-trialkylsulfoxonium salts.

The compounds of the formula (I) can form salts through adduct formation of a suitable inorganic or organic acid, for example mineral acids such as HCl, HBr, H₂SO₄, H₃PO₄ or HNO₃, or organic acids, for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, with a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as anion.

Preference is given to compounds of the general formula (I) where the symbols and indices have the following meanings:

-   -   Q is Q¹, Q², Q³ or Q⁴

-   -   R^(x) is Me, Et, Pr, i-Pr, c-Pr, (CH₂)₂OMe or Ph,     -   R^(y) is Cl, Me, Et or CF₃,     -   R^(z) is hydrogen, Me, Et or CF₃,     -   X is halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, c-Pr, OMe, OEt,         SMe, SEt, SO₂Me, SO₂Et, CH₂OMe, CH₂SMe, CH₂SO₂Me, (CH₂)₂SMe or         (CH₂)₂SO₂Me,     -   Y is halogen, halo-(C₁-C₆)-alkyl, OMe, SMe, S(O)Me, SO₂Me, SEt,         S(O)Et or SO₂Et,     -   Z is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, CH₂c-Pr,         halo-(C₁-C₆)-alkyl, (CH₂)₂OMe, (CH₂)₂OEt, allyl, propynyl,         (CH₂)₂SMe, (CH₂)₂SO₂Me, C(O)Me, C(O)cPr, C(O)OMe, C(O)OEt,         CH₂-(tetrahydrofuran-2-yl), oxetan-3-yl, CH₂C(O)Me, CH₂C(O)c-Pr,         CH₂C(O)NMe₂, CH₂CN, Ph, CH₂Ph or CH₂-(thien-2-yl), OMe, OEt,         OPr, Oi-Pr.

Particular preference is given to compounds of the general formula (I) where the symbols and indices have the following meanings:

-   -   Q is Q¹ or Q⁴,     -   R^(x) is Me, Et or Pr,     -   R^(z) is H or Me,     -   X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt, CH₂OMe or CF₃,     -   Y is F, Cl, Br, I, SMe, S(O)Me, SO₂Me, CF₃, CHF₂ or C₂F₅,     -   Z is hydrogen, Me, Et, c-Pr, Pr, i-Pr, c-Bu, CH₂-c-Pr, CH₂CHF₂,         CH₂CF₃, CH(Me)-c-Pr, (CH₂)₂OMe, (CH₂)₂SMe, CH₂CN,         CH₂-(tetrahydrofuran-2-yl), CH₂C(O)NMe₂, Ph or CH₂-(thien-2-yl),         oxetan-3-yl, OMe, OEt, OPr, Oi-Pr.

Compounds of the invention can be prepared, for example, by the method specified in Scheme 1 of WO 2012/028579 A1. The corresponding benzoyl chlorides or the parent benzoic acids thereof are known in principle and can be prepared, for example, by the methods described in WO1997/041105, WO1998/029383, WO1999/021852, EP282944, JP11021280, JP11012275 or CN103130730. The working examples described further down further elucidate the mode of preparation of the compounds of the invention.

The workup of the respective reaction mixtures is generally effected by known processes, for example by crystallization, aqueous-extractive workup, by chromatographic methods or by a combination of these methods.

Depending on the nature of the substituents and the manner in which they are attached, the compounds of the general formula (I) may be present as stereoisomers. If, for example, one or more asymmetrically substituted carbon atoms are present, there may be enantiomers and diastereomers. Stereoisomers likewise occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. It is likewise possible to selectively prepare stereoisomers by using stereoselective reactions with use of optically active starting materials and/or auxiliaries. The invention also relates to all the stereoisomers and mixtures thereof that are encompassed by the general formula (I) but are not defined specifically.

Collections of compounds of the formula (I) and/or salts thereof which can be synthesized by the abovementioned reactions can also be prepared in a parallelized manner, in which case this may be accomplished in a manual, partly automated or fully automated manner. It is possible, for example, to automate the conduct of the reaction, the workup or the purification of the products and/or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999, on pages 1 to 34.

The inventive compounds of the formula (I) (and/or salts thereof), referred to collectively as “compounds of the invention” hereinafter, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants.

The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which one or more compound(s) of the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or the area on which the plants grow (for example the area under cultivation). The compounds of the invention can be deployed, for example, prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds of the invention are as follows, though the enumeration is not intended to impose a restriction to particular species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

When the compounds of the invention are applied to the soil surface before germination, either the weed seedlings are prevented completely from emerging or the weeds grow until they have reached the cotyledon stage, but then stop growing.

If the active ingredients are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

The compounds of the invention can be selective in crops of useful plants and can also be employed as non-selective herbicides.

By virtue of their herbicidal and plant growth regulatory properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain active ingredients used in the agrochemical industry, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further particular properties lie in tolerance or resistance to abiotic stress factors, for example heat, cold, drought, salinity and ultraviolet radiation.

Preference is given to using the inventive compounds of the formula (I) or salts thereof in economically important transgenic crops of useful and ornamental plants.

The compounds of the formula (I) can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants.

Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP 0221044, EP 0131624). What have been described are, for example, several cases of genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/011376 A, WO 92/014827 A, WO 91/019806 A), transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf., for example, EP 0242236 A, EP 0242246 A) or of the glyphosate type (WO 92/000377 A) or of the sulfonylurea type (EP 0257993 A, U.S. Pat. No. 5,013,659) or to combinations or mixtures of these herbicides through “gene stacking”, such as transgenic crop plants, for example corn or soya with the trade name or the designation Optimum™ GAT™ (Glyphosate ALS Tolerant).

-   -   transgenic crop plants, for example cotton, capable of producing         Bacillus thuringiensis toxins (Bt toxins), which make the plants         resistant to particular pests (EP 0142924 A, EP 0193259 A),     -   transgenic crop plants having a modified fatty acid composition         (WO 91/013972 A),     -   genetically modified crop plants having novel constituents or         secondary metabolites, for example novel phytoalexins, which         cause an increase in disease resistance (EP 0309862 A, EP         0464461 A),     -   genetically modified plants having reduced photorespiration,         which have higher yields and higher stress tolerance (EP 0305398         A),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which feature higher yields or better         quality,     -   transgenic crop plants which are distinguished by a combination,         for example of the abovementioned novel properties (“gene         stacking”).

Numerous molecular biology techniques which can be used to produce novel transgenic plants with modified properties are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds), Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such genetic manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove part sequences or add natural or synthetic sequences. For the connection of the DNA fragments to one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants. Obtainable in this way are transgenic plants having properties altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

The compounds (I) of the invention can be used with preference in transgenic crops which are resistant to growth regulators, for example 2,4-D, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients, or to any desired combinations of these active ingredients.

The compounds of the invention can be used with particular preference in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones. Most preferably, the compounds of the invention can be used in transgenic crop plants such as corn or soya with the trade name or the designation Optimum™ GAT™ (glyphosate ALS tolerant), for example.

When the active ingredients of the invention are employed in transgenic crops, not only do the effects towards harmful plants observed in other crops occur, but frequently also effects which are specific to the application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the inventive compounds of the formula (I) as herbicides for controlling harmful plants in transgenic crop plants.

The compounds of the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant-growth-regulating compositions which comprise the compounds of the invention.

The compounds of the invention can be formulated in various ways, according to the biological and/or physicochemical parameters required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973, K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials, surfactants, solvents and further additives are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y., C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963, McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, “Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

On the basis of these formulations, it is also possible to produce combinations with other active ingredients, for example insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix.

Combination partners usable for the compounds of the invention in mixed formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as known, for example, from Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the following, where said active ingredients are referred to either by their “common name” in accordance with the International Organization for Standardization (ISO) or by the chemical name or by the code number. They always encompass all the use forms, for example acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not mentioned explicitly.

Examples of such herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alidochlore, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalm, chlorotoluron, chlorothal-dimethyl, chlorsulfuron, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, fluorenol, fluorenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetat, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxotrione (lancotrione), oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

Examples of plant growth regulators as possible mixing partners are:

acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, fluorenol, fluorenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

Safeners which can be used in combination with the inventive compounds of the formula (I) and optionally in combinations with further active ingredients such as insecticides, acaricides, herbicides, fungicides as listed above are preferably selected from the group consisting of:

-   -   S1) Compounds of the formula (S1)

-   -   where the symbols and indices have the meanings below:     -   n_(A) is a natural number from 0 to 5, preferably from 0 to 3;     -   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or         (C₁-C₄)-haloalkyl;     -   W_(A) is an unsubstituted or substituted divalent heterocyclic         radical from the group of the partly unsaturated or aromatic         five-membered heterocycles having 1 to 3 ring heteroatoms from         the N and O group, where at least one nitrogen atom and at most         one oxygen atom is present in the ring, preferably a radical         from the group of (W_(A) ¹) to (W_(A) ⁴),     -   m_(A) is 0 or 1;

R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to 3 heteroatoms, preferably from the group consisting of O and S, which is joined to the carbonyl group in (S1) via the nitrogen atom and is unsubstituted or substituted by radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or optionally substituted phenyl, preferably a radical of the formula OR_(A) ³, NHR_(A) ⁴ or N(CH₃)₂, especially of the formula OR_(A) ³

-   -   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic         hydrocarbon radical, preferably having a total of 1 to 18 carbon         atoms;     -   R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or         substituted or unsubstituted phenyl;     -   R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,         (C₁-C₄)-alkoxy-(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹, where     -   R_(A) ⁹ is hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,         (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,         (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl;     -   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are         hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl         or substituted or unsubstituted phenyl;     -   preferably:     -   a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid         type (S1^(a)), preferably compounds such as         1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic         acid, ethyl         1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate         (S1-1) (“mefenpyr-diethyl”), and related compounds as described         in WO-A-91/07874;     -   b) derivatives of dichlorophenylpyrazolecarboxylic acid         (S1^(b)), preferably compounds such as ethyl         1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2),         ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate         (S1-3), ethyl         1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate         (S1-4) and related compounds as described in EP-A-333 131 and         EP-A-269 806;     -   c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid         (S1^(c)), preferably compounds such as ethyl         1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5),         methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6)         and related compounds as described in EP-A-268 554, for example;     -   d) compounds of the triazolecarboxylic acid type (S1^(d)),         preferably compounds such as fenchlorazole(-ethyl ester), i.e.         ethyl         1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate         (S1-7), and related compounds as described in EP-A-174 562 and         EP-A-346 620;     -   e) compounds of the 5-benzyl- or         5-phenyl-2-isoxazoline-3-carboxylic acid or of the         5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1^(e)),         preferably compounds such as ethyl         5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (51-8) or         ethyl 5-phenyl-2-isoxazoline-3-carboxylate (51-9) and related         compounds as described in WO-A-91/08202, or         5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl         5,5-diphenyl-2-isoxazoline-3-carboxylate (51-11)         (“isoxadifen-ethyl”) or n-propyl         5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl         5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13),         as described in patent application WO-A-95/07897.     -   S2) Quinoline derivatives of the formula (S2)

-   -   where the symbols and indices have the meanings below:     -   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or         (C₁-C₄)-haloalkyl;     -   n_(B) is a natural number from 0 to 5, preferably from 0 to 3;     -   R_(B) ² is OR_(B) ³, SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated         or unsaturated 3- to 7-membered heterocycle having at least one         nitrogen atom and up to 3 heteroatoms, preferably from the group         of O and S, which is joined via the nitrogen atom to the         carbonyl group in (S2) and is unsubstituted or substituted by         radicals from the group of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or         optionally substituted phenyl, preferably a radical of the         formula OR_(B) ³, NHR_(B) ⁴ or N(CH₃)₂, especially of the         formula OR_(B) ³;     -   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic         hydrocarbon radical, preferably having a total of 1 to 18 carbon         atoms;     -   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or         substituted or unsubstituted phenyl;     -   T_(B) is a (C₁ or C₂)-alkanediyl chain which is unsubstituted or         substituted by one or two (C₁-C₄)-alkyl radicals or by         [(C₁-C₃)-alkoxy]carbonyl;     -   preferably:     -   a) compounds of the 8-quinolinoxyacetic acid type (S2a),         preferably     -   1-methylhexyl(5-chloro-8-quinolinoxy)acetate         (“cloquintocet-mexyl”) (S2-1),     -   (1,3-dimethylbut-1-yl) (5-chloro-8-quinolinoxy)acetate (S2-2),     -   4-allyloxybutyl(5-chloro-8-quinolinoxy)acetate (S2-3),     -   1-allyloxyprop-2-yl(5-chloro-8-quinolinoxy)acetate (S2-4),     -   ethyl(5-chloro-8-quinolinoxy)acetate (S2-5),     -   methyl (5-chloro-8-quinolinoxy)acetate (S2-6),     -   allyl(5-chloro-8-quinolinoxy)acetate (S2-7),     -   2-(2-propylideneiminoxy)-1-ethyl(5-chloro-8-quinolinoxy)acetate         (S2-8), 2-oxoprop-1-yl(5-chloro-8-quinolinoxy)acetate (S2-9) and         related compounds, as described in EP-A-86 750, EP-A-94 349 and         EP-A-191 736 or EP-A-0 492 366, and also         (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts         thereof, for example the lithium, sodium, potassium, calcium,         magnesium, aluminum, iron, ammonium, quaternary ammonium,         sulfonium or phosphonium salts thereof, as described in         WO-A-2002/34048;     -   b) compounds of the (5-chloro-8-quinolinoxy)malonic acid type         (S2^(b)), preferably compounds such as         diethyl(5-chloro-8-quinolinoxy)malonate,         diallyl(5-chloro-8-quinolinoxy)malonate, methyl         ethyl(5-chloro-8-quinolinoxy)malonate and related compounds, as         described in EP-A-0 582 198.     -   S3) Compounds of the formula (S3)

-   -   where the symbols and indices are defined as follows:

R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl;

R_(C) ², R_(C) ³ are identical or different and are hydrogen, (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl, (C₁-C₄)alkylcarbamoyl-(C₁-C₄)alkyl, (C₂-C₄)alkenylcarbamoyl-(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, dioxolanyl-(C₁-C₄)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R_(C) ² and R_(C) ³ together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;

-   -   preferably:

active ingredients of the dichloroacetamide type, which are frequently used as pre-emergence safeners (soil-acting safeners), for example

-   -   “dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),     -   “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine)         from Stauffer (S3-2),     -   “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from         Stauffer (S3-3),     -   “benoxacor”         (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine)         (S3-4),     -   “PPG-1292”         (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from         PPG Industries (S3-5),     -   “DKA-24”         (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from         Sagro-Chem (S3-6),     -   “AD-67” or “MON 4660”         (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia         or Monsanto (S3-7),     -   “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),         “diclonon” (dicyclonon) or “BAS145138” or “LAB145138” (S3-9)     -   ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one)         from BASF,     -   “furilazole” or “MON 13900”         ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine)         (S3-10); and the (R) isomer thereof (S3-11).     -   S4) N-acylsulfonamides of the formula (S4) and salts thereof,

-   -   in which the symbols and indices are defined as follows:     -   A_(D) is SO₂—NR_(D) ³-CO or CO—NR_(D) ³-SO₂     -   X_(D) is CH or N;     -   R_(D) ¹ is CO—NR_(D) ⁵R_(D) ⁶ or NHCO—R_(D) ⁷;     -   R_(D) ² is halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,         nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulfonyl,         (C₁-C₄)-alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl;     -   R_(D) ³ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or         (C₂-C₄)-alkynyl;     -   R_(D) ⁴ is halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-haloalkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy,         cyano, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,         (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkoxycarbonyl or         (C₁-C₄)-alkylcarbonyl;     -   R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl, phenyl         or 3- to 6-membered heterocyclyl containing v_(D) heteroatoms         from the group consisting of nitrogen, oxygen and sulfur, where         the seven latter radicals are substituted by v_(D) substituents         from the group consisting of halogen, (C₁-C₆)-alkoxy,         (C₁-C₆)-haloalkoxy, (C₁-C₂)-alkylsulfinyl,         (C₁-C₂)-alkylsulfonyl, (C₃-C₆)-cycloalkyl,         (C₁-C₄)-alkoxycarbonyl, (C₁-C₄)-alkylcarbonyl and phenyl and, in         the case of cyclic radicals, also (C₁-C₄)-alkyl and         (C₁-C₄)-haloalkyl;     -   R_(D) ⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or         (C₂-C₆)-alkynyl, where the three latter radicals are substituted         by v_(D) radicals from the group consisting of halogen,         hydroxyl, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-alkylthio,         or     -   R_(D) ⁵ and R_(D) ⁶ together with the nitrogen atom carrying         them form a pyrrolidinyl or piperidinyl radical;     -   R_(D) ⁷ is hydrogen, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,         (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 latter radicals         are substituted by v_(D) substituents from the group consisting         of halogen, (C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy and         (C₁-C₄)-alkylthio and, in the case of cyclic radicals, also         (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;     -   n_(D) is 0, 1 or 2;     -   m_(D) is 1 or 2;     -   v_(D) is 0, 1, 2 or 3;     -   among these, preference is given to compounds of the         N-acylsulfonamide type, for example of the formula (S4a) below,         which are known, for example, from WO-A-97/45016

-   -   in which     -   R_(D) ⁷ is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 latter         radicals are substituted by v_(D) substituents from the group         consisting of halogen, (C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy and         (C₁-C₄)-alkylthio and, in the case of cyclic radicals, also         (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;     -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃;     -   m_(D) is 1 or 2;     -   v_(D) is 0, 1, 2 or 3;     -   and also     -   acylsulfamoylbenzamides, for example of the formula (S4^(b))         below, which are known, for example, from WO-A-99/16744,

-   -   e.g. those in which     -   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=2-OMe (“cyprosulfamide”,         S4-1),     -   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-2),     -   R_(D) ⁵=ethyl and (R_(D) ⁴)=2-OMe (S4-3),     -   R_(D) ⁵=isopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-4) and     -   R_(D) ⁵=isopropyl and (R_(D) ⁴)=2-OMe (S4-5)     -   and also     -   compounds of the N-acylsulfamoylphenylurea type of the formula         (S4^(c)), which are known, for example, from EP-A-365484,

-   -   in which     -   R_(D) ⁸ and R_(D) ⁹ are independently hydrogen, (C₁-C₈)-alkyl,         (C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl,     -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃,     -   m_(D) is 1 or 2;     -   for example     -   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea         (“metcamifen”, S4-6),         1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,         1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,     -   and also     -   N-phenylsulfonylterephthalamides of the formula (S4^(d)), which         are known, for example, from CN 101838227,

-   -   e.g. those in which     -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃;     -   m_(D) is 1 or 2;     -   R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,         (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl.     -   S5) Active ingredients from the class of the hydroxyaromatics         and the aromatic-aliphatic carboxylic acid derivatives (S5), for         example     -   ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic         acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,         4-fluorosalicylic acid, 2-hydroxycinnamic acid,         2,4-dichlorocinnamic acid, as described in WO-A-2004/084631,         WO-A-2005/015994, WO-A-2005/016001.     -   S6) Active ingredients from the class of the         1,2-dihydroquinoxalin-2-ones (S6), for example     -   1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,         1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,         1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one         hydrochloride,         1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,         as described in WO-A-2005/112630.     -   S7) Compounds of the formula (S7), as described in         WO-A-1998/38856,

-   -   in which the symbols and indices are defined as follows:     -   R_(E) ¹, R_(E) ² are independently halogen, (C₁-C₄)-alkyl,         (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkylamino,         di-(C₁-C₄)-alkylamino, nitro;     -   A_(E) is COOR_(E) ³ or COSR_(E) ⁴     -   R_(E) ³, R_(E) ⁴ are independently hydrogen, (C₁-C₄)-alkyl,         (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl, (C₁-C₄)-haloalkyl,         phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and         alkylammonium,     -   n_(E) is 0 or 1     -   n_(E) ², n_(E) ³ are independently 0, 1 or 2,     -   preferably:     -   diphenylmethoxyacetic acid,     -   ethyl diphenylmethoxyacetate,     -   methyl diphenylmethoxyacetate (CAS reg. no. 41858-19-9) (57-1).     -   S8) Compounds of the formula (S8), as described in         WO-A-98/27049,     -   in which

-   -   X_(F) is CH or N,     -   n_(F) in the case that X_(F)═N is an integer from 0 to 4 and in         the case that X_(F)═CH is an integer from 0 to 5,     -   R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,         (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkoxycarbonyl, optionally         substituted phenyl, optionally substituted phenoxy,     -   R_(F) ² is hydrogen or (C₁-C₄)-alkyl,     -   R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,         (C₂-C₄)-alkynyl or aryl, where each of the abovementioned         carbon-containing radicals is unsubstituted or substituted by         one or more, preferably up to three identical or different         radicals from the group consisting of halogen and alkoxy; or         salts thereof,     -   preferably compounds in which     -   X_(F) is CH,     -   n_(F) is an integer from 0 to 2,     -   R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,         (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,     -   R_(F) ² is hydrogen or (C₁-C₄)-alkyl,     -   R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,         (C₂-C₄)-alkynyl or aryl, where each of the abovementioned         carbon-containing radicals is unsubstituted or substituted by         one or more, preferably up to three identical or different         radicals from the group consisting of halogen and alkoxy,     -   or salts thereof.     -   S9) Active ingredients from the class of the         3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example     -   1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone         (CAS reg. no. 219479-18-2),         1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone         (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.     -   S10) Compounds of the formulae (S10^(a)) or (S10^(b))         -   as described in WO-A-2007/023719 and WO-A-2007/023764

-   -   in which     -   R_(G) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃,         OCF₃,     -   Y_(G), Z_(G) independently of one another represent O or S,     -   n_(G) is an integer from 0 to 4,     -   R_(G) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,         aryl; benzyl, halobenzyl,     -   R_(G) ³ is hydrogen or (C₁-C₆)-alkyl.     -   S11) Active ingredients of the oxyimino compounds type (S11),         which are known as seed-dressing agents, for example     -   “oxabetrinil”         ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1),         which is known as a seed-dressing safener for millet/sorghum         against metolachlor damage,     -   “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone         O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a         seed-dressing safener for millet/sorghum against metolachlor         damage, and     -   “cyometrinil” or “CGA-43089”         ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is         known as a seed-dressing safener for millet/sorghum against         metolachlor damage.     -   S12) Active ingredients from the class of the isothiochromanones         (S12), for example methyl         [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS         Reg. No. 205121-04-6) (S12-1) and related compounds from         WO-A-1998/13361.     -   S13) One or more compounds from group (S13):     -   “naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride)         (S13-1), which is known as a seed-dressing safener for corn         against thiocarbamate herbicide damage,     -   “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is         known as a safener for pretilachlor in sown rice,     -   “flurazole” (benzyl         2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3),         which is known as a seed-dressing safener for millet/sorghum         against alachlor and metolachlor damage,     -   “CL 304415” (CAS Reg. No. 31541-57-8)     -   (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4)         from American Cyanamid, which is known as a safener for corn         against damage by imidazolinones,     -   “MG 191” (CAS Reg. No. 96420-72-3)         (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from         Nitrokemia, which is known as a safener for corn,     -   “MG 838” (CAS Reg. No. 133993-74-5)     -   (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate)         (S13-6) from Nitrokemia,     -   “disulfoton” (0,0-diethyl S-2-ethylthioethyl phosphorodithioate)         (S13-7),     -   “dietholate” (0,0-diethyl O-phenyl phosphorothioate) (S13-8),     -   “mephenate” (4-chlorophenyl methylcarbamate) (S13-9).     -   S14) Active ingredients which, in addition to herbicidal action         against harmful plants, also have safener action on crop plants         such as rice, for example     -   “dimepiperate” or “MY 93” (S-1-methyl         1-phenylethylpiperidine-1-carbothioate), which is known as a         safener for rice against damage by the herbicide molinate,     -   “daimuron” or “SK 23”         (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a         safener for rice against damage by the herbicide imazosulfuron,     -   “cumyluron”=“JC 940”         (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see         JP-A-60087254), which is known as safener for rice against         damage by some herbicides,     -   “methoxyphenone” or “NK 049”         (3,3′-dimethyl-4-methoxybenzophenone), which is known as a         safener for rice against damage by some herbicides,     -   “CSB” (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai,         (CAS Reg. No. 54091-06-4), which is known as a safener against         damage by some herbicides in rice.     -   S15) Compounds of the formula (S15) or tautomers thereof

-   -   as described in WO-A-2007/131861 and WO-A-2008/131860 in which     -   R_(H) ¹ is a (C₁-C₆)-haloalkyl radical and     -   R_(H) ² is hydrogen or halogen and     -   R_(H) ³, R_(H) ⁴ are independently hydrogen, (C₁-C₁₆)-alkyl,         (C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl,

where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]amino, [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,

or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring,

where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]amino, [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,

-   -   or     -   R_(H) ³ is (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy,         (C₂-C₆)-alkynyloxy or (C₂-C₄)-haloalkoxy and     -   R_(H) ⁴ is hydrogen or (C₁-C₄)-alkyl or     -   R_(H) ³ and R_(H) ⁴ together with the directly attached nitrogen         atom represent a four- to eight-membered heterocyclic ring         which, as well as the nitrogen atom, may also contain further         ring heteroatoms, preferably up to two further ring heteroatoms         from the group of N, O and S, and which is unsubstituted or         substituted by one or more radicals from the group of halogen,         cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,         (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio.     -   S16) Active compounds which are used primarily as herbicides but         also have safener action on crop plants, for example     -   (2,4-dichlorophenoxy)acetic acid (2,4-D),     -   (4-chlorophenoxy)acetic acid,     -   (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),     -   4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),     -   (4-chloro-o-tolyloxy)acetic acid (MCPA),     -   4-(4-chloro-o-tolyloxy)butyric acid,     -   4-(4-chlorophenoxy)butyric acid,     -   3,6-dichloro-2-methoxybenzoic acid (dicamba),     -   1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate         (lactidichloro-ethyl).

Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid and metcamifen.

Wettable powders are preparations uniformly dispersible in water which, in addition to the active ingredient and apart from a diluent or inert substance, also comprise surfactants of ionic and/or nonionic type (wetting agent, dispersant), e.g. polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol poly glycolethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the active herbicidal ingredients are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active ingredient with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may be produced, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as already listed above, for example, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

Granules can be produced either by spraying the active ingredient onto granular inert material capable of adsorption or by applying active ingredient concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.

Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1% to 99% by weight, especially 0.1% to 95% by weight, of compounds of the invention. In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active ingredient concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active ingredient, preferably usually 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends partially on whether the active ingredient is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active ingredient is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

In addition, the active ingredient formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity.

On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix.

For application, the formulations in the commercial form are diluted if appropriate in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in dust form, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

The required application rate of the compounds of the formula (I) and their salts varies according to the external conditions such as, inter alia, temperature, humidity and the type of herbicide used. It can vary within wide limits, for example between 0.001 and 10.0 kg/ha or more of active substance, but it is preferably between 0.005 and 5 kg/ha, more preferably in the range of from 0.01 to 1.5 kg/ha, more preferably in the range of from 0.05 to 1 kg/ha. This applies both to pre-emergence and to post-emergence application.

A carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed. The carrier, which may be solid or liquid, is generally inert and should be suitable for use in agriculture. Useful solid or liquid carriers include: for example ammonium salts and natural rock dusts, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock dusts, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils, and derivatives thereof. It is likewise possible to use mixtures of such carriers. Useful solid carriers for granules include: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.

Suitable liquefied gaseous extenders or carriers are liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide.

In the formulations, it is possible to use tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Further additives may be mineral and vegetable oils.

When the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and also water.

The compositions of the invention may additionally comprise further components, for example surfactants. Useful surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolyzates, lignosulfite waste liquors and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and when application is effected in water. The proportion of surfactants is between 5 and 40 percent by weight of the inventive composition. It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

If appropriate, it is also possible for other additional components to be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestrants, complexing agents. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes. In general, the compositions and formulations of the invention contain between 0.05% and 99% by weight, 0.01% and 98% by weight, preferably between 0.1% and 95% by weight, more preferably between 0.5% and 90% active ingredient, most preferably between 10 and 70 percent by weight. The active ingredients or compositions of the invention can be used as such or, depending on their respective physical and/or chemical properties, in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold-fogging concentrates, warm-fogging concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seed, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, pastes, pesticide coated seed, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, sprayable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for the treatment of seed, wettable powders, natural products and synthetic substances impregnated with active ingredient, and also microencapsulations in polymeric substances and in coating materials for seed, and also ULV cold-fogging and warm-fogging formulations.

The formulations mentioned can be produced in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixative, wetting agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, antifoams, preservatives, secondary thickeners, tackifiers, gibberellins and other processing auxiliaries.

The compositions of the invention include not only formulations which are already ready for use and can be deployed with a suitable apparatus onto the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.

The active ingredients of the invention may be present as such or in their (commercial standard) formulations, or else in the use forms prepared from these formulations as a mixture with other (known) active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or semiochemicals.

The inventive treatment of the plants and plant parts with the active ingredients or compositions is effected directly or by action on their surroundings, habitat or storage space by the customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, watering (drenching), drip irrigating and, in the case of propagation material, especially in the case of seeds, also by dry seed treatment, wet seed treatment, slurry treatment, incrustation, coating with one or more coats, etc. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.

One of the advantages of the present invention is that the particular systemic properties of the inventive active ingredients and compositions mean that treatment of the seed with these active ingredients and compositions protects not only the seed itself but also the resulting plants after emergence from phytopathogenic fungi. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.

It is likewise considered to be advantageous that the inventive active ingredients or compositions can especially also be used for transgenic seed, in which case the plant which grows from this seed is capable of expressing a protein which acts against pests. The treatment of such seed with the inventive active ingredients or compositions, merely through the expression of the protein, for example an insecticidal protein, can result in control of certain pests. Surprisingly, a further synergistic effect can be observed in this case, which additionally increases the effectiveness for protection against attack by pests.

The compositions of the invention are suitable for protection of seed of any plant variety which is used in agriculture, in the greenhouse, in forests or in horticulture and viticulture. In particular, this is the seed of cereals (such as wheat, barley, rye, triticale, sorghum/millet and oats), corn, cotton, soya beans, rice, potatoes, sunflower, bean, coffee, beet (for example sugar beet and fodder beet), peanut, oilseed rape, poppy, olive, coconut, cocoa, sugar cane, tobacco, vegetables (such as tomato, cucumbers, onions and lettuce), turf and ornamentals (see also below). The treatment of the seed of cereals (such as wheat, barley, rye, triticale and oats), corn and rice is of particular importance.

As also described below, the treatment of transgenic seed with the active ingredients or compositions of the invention is of particular significance. This relates to the seed of plants containing at least one heterologous gene which enables the expression of a polypeptide or protein having insecticidal properties. The heterologous gene in transgenic seed can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. This heterologous gene preferably originates from Bacillus sp., in which case the gene product is effective against the European corn borer and/or the Western corn rootworm. The heterologous gene more preferably originates from Bacillus thuringiensis.

In the context of the present invention, the inventive composition is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, the seed can be treated at any time between harvest and sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again.

In general, when treating the seed, it has to be ensured that the amount of the composition of the invention and/or further additives applied to the seed is chosen such that the germination of the seed is not impaired and the plant which arises therefrom is not damaged. This has to be ensured particularly in the case of active ingredients which can exhibit phytotoxic effects at certain application rates.

The compositions of the invention can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: U.S. Pat. Nos. 4,272,417 A, 4,245,432 A, U.S. Pat. Nos. 4,808,430, 5,876,739, U.S. 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.

The active ingredients which can be used in accordance with the invention can be converted to the customary seed-dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.

These formulations are produced in a known manner, by mixing the active ingredients with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed-dressing formulations usable in accordance with the invention are all substances which promote wetting and which are customary for the formulation of agrochemically active ingredients. Alkyl naphthalenesulfonates, such as diisopropyl or diisobutyl naphthalenesulfonates, can be used with preference.

Suitable dispersants and/or emulsifiers which may be present in the seed-dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemically active ingredients. Preference can be given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and the phosphated or sulfated derivatives thereof. Suitable anionic dispersants are especially lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usable in accordance with the invention are all foam-inhibiting substances customary for the formulation of agrochemically active ingredients. Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulations usable in accordance with the invention are all customary binders usable in seed-dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The seed-dressing formulations usable in accordance with the invention can be used, either directly or after previously having been diluted with water, for the treatment of a wide range of different seed, including the seed of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.

For the treatment of seed with the seed-dressing formulations usable in accordance with the invention or with the preparations prepared therefrom by addition of water, useful equipment is all mixing units usable customarily for seed dressing. Specifically, the seed dressing procedure is to place the seed into a mixer, to add the particular desired amount of seed-dressing formulations, either as such or after prior dilution with water, and to mix them until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying operation.

The active ingredients of the invention, given good plant compatibility, favorable homeotherm toxicity and good environmental compatibility, are suitable for protection of plants and plant organs, for increasing harvest yields, and for improving the quality of the harvested crop. They can preferably be used as crop protection agents. They are active against normally sensitive and resistant species and also against all or specific stages of development.

Plants which can be treated in accordance with the invention include the following main crop plants: corn, soybean, cotton, Brassica oil seeds such as Brassica napus (e.g. Canola), Brassica rapa, B. juncea (e.g. (field) mustard) and Brassica carinata, rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, grapes and various fruit and vegetables from various botanic taxa, for example Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and berry fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes, potatoes, peppers, aubergines), Liliaceae sp., Compositae sp. (for example lettuce, artichokes and chicory—including root chicory, endive or common chicory), Umbelliferae sp. (for example carrots, parsley, celery and celeriac), Cucurbitaceae sp. (for example cucumbers—including gherkins, pumpkins, watermelons, calabashes and melons), Alliaceae sp. (for example leeks and onions), Cruciferae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and chinese cabbage), Leguminosae sp. (for example peanuts, peas, and beans—for example common beans and broad beans), Chenopodiaceae sp. (for example Swiss chard, fodder beet, spinach, beetroot), Malvaceae (for example okra), Asparagaceae (for example asparagus); useful plants and ornamental plants in the garden and woods; and in each case genetically modified types of these plants.

As mentioned above, it is possible to treat all plants and their parts in accordance with the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding techniques, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof are treated. The term “parts” or “parts of plants” or “plant parts” has been explained above. Particular preference is given in accordance with the invention to treating plants of the respective commercially customary plant cultivars or those that are in use. Plant cultivars are understood to mean plants having new properties (“traits”) which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may be cultivars, varieties, biotypes and genotypes.

The treatment method of the invention can be used for the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term “heterologous gene” means essentially a gene which is provided or assembled outside the plant and which, upon introduction into the nuclear genome, the chloroplast genome or the mitochondrial genome, imparts to the transformed plant novel or improved agronomical or other traits because it expresses a protein or polypeptide of interest or another gene which is present in the plant, or other genes which are present in the plant are down-regulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA interference]). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its specific presence in the plant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the inventive treatment may also result in superadditive (“synergistic”) effects. For example, the following effects which exceed the effects actually to be expected are possible: reduced application rates and/or widened spectrum of activity and/or increased efficacy of the active ingredients and compositions which can be used in accordance with the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, greater plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products.

At certain application rates, the inventive active ingredient combinations may also have a fortifying effect on plants. Accordingly, they are suitable for mobilizing the defense system of the plant against attack by unwanted phytopathogenic fungi and/or microorganisms and/or viruses. This may possibly be one of the reasons for the enhanced activity of the inventive combinations for example against fungi. Plant-fortifying (resistance-inducing) substances shall be understood to mean, in the present context, also those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted phytopathogenic fungi, the plants treated display a substantial degree of resistance to these unwanted phytopathogenic fungi. The inventive substances can therefore be used for protection of plants from attack by the pathogens mentioned within a certain period of time after treatment. The period within which protection is achieved generally extends for from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active ingredients.

Plants and plant cultivars which are preferably treated in accordance with the invention include all plants which have genetic material which imparts particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).

Plants and plant cultivars which are likewise preferably treated in accordance with the invention are resistant to one or more biotic stress factors, meaning that these plants have a better defense against animal and microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Examples of nematode-resistant plants are described, for example, in the following U.S. patent application Ser. Nos. 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947, 12/252,453, 12/209,354, 12/491,396 and 12/497,221.

Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, exposure to ozone, exposure to strong light, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients or lack of shade.

Plants and plant varieties which may also be treated according to the invention are those plants characterized by enhanced yield characteristics. Enhanced yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can also be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and oil composition, nutritional value, reduction in antinutritional compounds, improved processability and better storage stability.

Plants that may be treated according to the invention are hybrid plants that already express the characteristics of heterosis, or hybrid effect, which results generally in higher yield, vigour, better health and resistance towards biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male-sterile parent line (the female crossbreeding parent) with another inbred male-fertile parent line (the male crossbreeding parent). Hybrid seed is typically harvested from the male-sterile plants and sold to growers. Male-sterile plants can sometimes (e.g. in maize) be produced by detasseling (i.e. the mechanical removal of the male reproductive organs or male flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be harvested from the hybrid plants, it is typically beneficial to ensure that male fertility in hybrid plants, which contain the genetic determinants responsible for male sterility, is fully restored. This can be accomplished by ensuring that the male crossbreeding parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described for Brassica species. However, genetic determinants for male sterility can also be located in the nuclear genome. Male-sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 89/10396 in which, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate by various methods. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science, 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genes encoding a petunia EPSPS (Shah et al., 1986, Science 233, 478-481), a tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or an Eleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the abovementioned genes. Plants which express EPSPS genes which impart glyphosate tolerance have been described. Plants which express other genes which impart glyphosate tolerance, for example decarboxylase genes, have been described.

Other herbicide-resistant plants are for example plants made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant of the glutamine synthase enzyme that is resistant to inhibition. One example of such an effective detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase have been described.

Further herbicide-tolerant plants are also plants that have been made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated or chimeric HPPD enzyme, as described in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or U.S. Pat. No. 6,768,044. Tolerance to HPPD inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928. In addition, plants can be made more tolerant to HPPD inhibitors by inserting into the genome thereof a gene which encodes an enzyme which metabolizes or degrades HPPD inhibitors, for example CYP450 enzymes (see WO 2007/103567 and WO 2008/150473).

Other herbicide-resistant plants are plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. It is known that different mutations in the ALS enzyme (also known as acetohydroxy acid synthase, AHAS) confer tolerance to different herbicides and groups of herbicides, as described, for example, in Tranel and Wright (Weed Science 2002, 50, 700-712). The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants has been described. Further sulfonylurea- and imidazolinone-tolerant plants have also been described.

Further plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, by selection in cell cultures in the presence of the herbicide or by mutation breeding (cf., for example, for soya beans U.S. Pat. No. 5,084,082, for rice WO 97/41218, for sugar beet U.S. Pat. No. 5,773,702 and WO 99/057965, for lettuce U.S. Pat. No. 5,198,599 or for sunflower WO 01/065922).

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.

In the present context, the term “insect-resistant transgenic plant” includes any plant containing at least one transgene comprising a coding sequence encoding the following:

1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins compiled by Crickmore et al. (Microbiology and Molecular Biology Reviews 1998, 62, 807-813), updated by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, for example proteins of the Cry protein classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP-A 1999141 and WO 2007/107302), or those proteins encoded by synthetic genes as described in U.S. patent application Ser. No. 12/249,016; or

2) a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second crystal protein other than Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cy34 and Cy35 crystal proteins (Nat. Biotechnol. 2001, 19, 668-72; Applied Environm. Microbiol. 2006, 71, 1765-1774) or the binary toxin made up of the Cry1A or Cry1F proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S. patent application Ser. No. 12/214,022 and EP08010791.5); or

3) a hybrid insecticidal protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, for example the Cry1A.105 protein produced by corn event MON98034 (WO 2007/027777); or

4) a protein of any one of 1) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A protein in corn event MIR604; or

5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal proteins (VIP) listed at: http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html, for example proteins from the VIP3Aa protein class; or

6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 94/21795); or

7) a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or

8) a protein of any one of points 5) to 7) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes induced in the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT 102; or

9) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a crystal protein from Bacillus thuringiensis, such as the binary toxin made up of the proteins VIP3 and Cry1A or Cry1F (U.S. patent applications 61/126,083 and 61/195,019), or the binary toxin made up of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S. patent application Ser. No. 12/214,022 and EP 08010791.5); or

10) a protein according to point 9) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes induced in the encoding DNA during cloning or transformation (while still encoding an insecticidal protein).

Of course, insect-resistant transgenic plants, as used herein, also include any plant comprising a combination of genes encoding the proteins of any one of the abovementioned classes 1 to 10. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 10, to expand the range of the target insect species affected or to delay insect resistance development to the plants, by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.

In the present context, an “insect-resistant transgenic plant” additionally includes any plant containing at least one transgene comprising a sequence for production of double-stranded RNA which, after consumption of food by an insect pest, prevents the growth of this pest.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stress factors. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress-tolerant plants include the following:

a. plants which contain a transgene capable of reducing the expression and/or the activity of the poly(ADP-ribose) polymerase (PARP) gene in the plant cells or plants;

b. plants which contain a stress tolerance-enhancing transgene capable of reducing the expression and/or the activity of the PARG-encoding genes of the plants or plant cells;

c. plants which contain a stress tolerance-enhancing transgene coding for a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthesis pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage stability of the harvested product and/or altered properties of specific components of the harvested product such as, for example:

1) Transgenic plants which synthesize a modified starch which, in its physicochemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behavior, the gelling strength, the starch granule size and/or the starch granule morphology, is changed in comparison with the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited to specific applications.

2) Transgenic plants which synthesize non-starch carbohydrate polymers or which synthesize non-starch carbohydrate polymers with altered properties in comparison to wild-type plants without genetic modification. Examples are plants which produce polyfructose, especially of the inulin and levan type, plants which produce alpha-1,4-glucans, plants which produce alpha-1,6-branched alpha-1,4-glucans, and plants producing alternan.

3) Transgenic plants which produce hyaluronan.

4) Transgenic plants or hybrid plants such as onions with particular properties, such as “high soluble solids content”, “low pungency” (LP) and/or “long storage” (LS).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such altered fiber characteristics and include:

a) plants, such as cotton plants, containing an altered form of cellulose synthase genes;

b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants with an increased expression of sucrose phosphate synthase;

c) plants, such as cotton plants, with increased expression of sucrose synthase;

d) plants, such as cotton plants, wherein the timing of the plasmodesmatal gating at the base of the fiber cell is altered, for example through downregulation of fiber-selective β-1,3-glucanase;

e) plants, such as cotton plants, which have fibres with altered reactivity, for example through expression of the N-acetylglucosaminetransferase gene, including nodC, and chitin synthase genes.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such altered oil characteristics and include:

a) plants, such as oilseed rape plants, which produce oil having a high oleic acid content;

b) plants, such as oilseed rape plants, which produce oil having a low linolenic acid content;

c) plants, such as oilseed rape plants, which produce oil having a low level of saturated fatty acids.

Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants such as potatoes which are virus-resistant, for example to the potato virus Y (SY230 and SY233 events from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (e.g. RB gene), or which exhibit reduced cold-induced sweetness (which bear the genes Nt-Inh, II-INV) or which exhibit the dwarf phenotype (A-20 oxidase gene).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such altered characteristics, and include plants such as oilseed rape with retarded or reduced seed shattering.

Particularly useful transgenic plants which can be treated according to the invention are plants with transformation events or combinations of transformation events which are the subject of granted or pending petitions for nonregulated status in the USA at the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA). Information relating to this is available at any time from APHIS (4700 River Road Riverdale, Md. 20737, USA), for example via the website http://www.aphis.usda.gov/brs/not_reg.html. At the filing date of this application, the petitions with the following information were either granted or pending at APHIS:

-   -   Petition: Identification number of the petition. The technical         description of the transformation event can be found in the         specific petition document available from APHIS on the website         via the petition number. These descriptions are hereby disclosed         by reference.     -   Extension of a petition: Reference to an earlier petition for         which an extension of scope or term is being requested.     -   Institution: Name of the person submitting the petition.     -   Regulated article: The plant species in question.     -   Transgenic phenotype: The trait imparted to the plant by the         transformation event.     -   Transformation event or line: The name of the event(s)         (sometimes also referred to as line(s)) for which nonregulated         status is being requested.     -   APHIS documents: Various documents which have been published by         APHIS with regard to the petition or can be obtained from APHIS         on request.

Particularly useful transgenic plants which can be treated in accordance with the invention are plants which comprise one or more genes which code for one or more toxins, for example the transgenic plants which are sold under the following trade names: YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example maize), Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned include maize varieties, cotton varieties and soya bean varieties which are available under the following trade names: Roundup Ready® (tolerance to glyphosates, for example corn, cotton, soya beans), Liberty Link® (tolerance to phosphinothricin, for example oilseed rape), IMI® (tolerance to imidazolinone) and SCS® (tolerance to sulfonylurea), for example corn. Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example corn).

Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or a combination of transformation events, and that are listed for example in the databases for various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://cera-gmc.org/index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit).

The active ingredients or compositions of the invention can also be used in the protection of materials, for protection of industrial materials against attack and destruction by unwanted microorganisms, for example fungi and insects.

In addition, the compounds of the invention can be used as antifouling compositions, alone or in combinations with other active ingredients.

Industrial materials in the present context are understood to mean non-living materials which have been prepared for use in industry. For example, industrial materials which are to be protected by active ingredients of the invention from microbial alteration or destruction may be adhesives, sizes, paper, wallpaper and cardboard, textiles, carpets, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. The range of materials to be protected also includes parts of production plants and buildings, for example cooling water circuits, cooling and heating systems, and ventilation and air conditioning systems, which may be impaired by the proliferation of microorganisms. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood. The active ingredients or compositions of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mold. In addition, the compounds of the invention can be used for protection of objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signaling systems, from fouling.

The method of the invention for controlling unwanted fungi can also be employed for protecting storage goods. “Storage goods” are understood to mean natural substances of vegetable or animal origin or processing products thereof of natural origin, for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, whether unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The active ingredients of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mold.

Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: Diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, for example Puccinia recondita or Puccinia triticina; Uromyces species, for example Uromyces appendiculatus; diseases caused by pathogens from the group of the Oomycetes, for example Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladosporium species, for example Cladosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium); Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerella graminicola and M. fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres; Ramularia species, for example Ramularia collo-cygni; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis; root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Rhizoctonia species, for example Rhizoctonia solani; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; ear and panicle diseases (including corn crops) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium spp.; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Septoria species, for example Septoria nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries, T. controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda, U. nuda tritici; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum and P. purpurogenum; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticillium species, for example Verticillium alboatrum; seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Fusarium species, for example Fusarium culmorum; Phytophthora species, for example Phytophthora cactorum; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Sclerotium species, for example Sclerotium rolfsii; cancerous diseases, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena;

wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa; deformations of leaves, flowers and fruits caused, for example, by Taphrina species, for example Taphrina deformans; degenerative diseases of woody plants caused, for example, by Esca species, for example Phaemoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea; diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea; diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani; diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora.

The following diseases of soya beans can be controlled with preference:

Fungal diseases on leaves, stems, pods and seeds caused, for example, by alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllosticta leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), Rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), Stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus root rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), Phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), Sclerotinia stem decay (Sclerotinia sclerotiorum), Sclerotinia southern blight (Sclerotinia rolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The active ingredients of the invention preferably act against fungi, especially molds, wood-discoloring and wood-destroying fungi (Basidiomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.

In addition, the active ingredients of the invention also have very good antimycotic activity. They have a very broad antimycotic activity spectrum, in particular against dermatophytes and yeasts, molds and diphasic fungi, (for example against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The enumeration of these fungi in no way constitutes a restriction of the mycotic spectrum that can be controlled, and is merely of illustrative character.

The active ingredients of the invention can therefore be used both in medical and in non-medical applications.

If appropriate, the compounds of the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). They can, as the case may be, also be used as intermediates or precursors for the synthesis of further active ingredients.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES Synthesis of 4-bromo-2-chloro-N³-ethyl-N¹-(1-methyl-1H-tetrazol-5-yl)isophthalamide (Example No. 1-178) Step 1: Preparation of 6-bromo-2-chloro-3-(methoxycarbonyl)benzoic Acid

1.47 g (5.29 mmol) of methyl 4-bromo-2-chloro-3-formylbenzoate was initially charged 100 ml of acetone. A solution of 636 mg (6.35 mmol) of chromium(VI) oxide in dilute sulfuric acid (H₂O:H₂SO₄ 3:1) was slowly added dropwise. The mixture was warmed to room temperature and stirred for 12 hours. Thereafter, a little isopropanol was added and the mixture was concentrated under reduced pressure. The residue was taken up in water and extracted with ethyl acetate, and the organic phase was dried and concentrated to dryness. 1.23 g of 6-bromo-2-chloro-3-(methoxycarbonyl)benzoic acid was obtained.

¹H-NMR (400 MHz, DMSO-d₆): δ=14.30 (br s, 1H); 7.82 (d, 1H); 7.77 (d, 1H); 3.88 (s, 3H).

Step 2: Preparation of methyl 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoate

To an initial charge of 753 mg (2.56 mmol) of 6-bromo-2-chloro-3-(methoxycarbonyl)benzoic acid in 30 ml dichloromethane were added catalytic amounts of dimethylformamide. Thereafter, at room temperature, 490 mg (3.84 mmol) of oxalyl chloride was added and the mixture was stirred for a further 1 hour. The mixture was concentrated to dryness, and the residue was coevaporated with toluene. The resulting residue was taken up in 5 ml of dichloromethane. To an initial charge of 1.9 ml (3.84 mmol) of a 2.5M solution of ethylamine in tetrahydrofuran and 663 mg (5.13 mmol) of Hünig's base in 50 ml dichloromethane was added, at 0° C., the acid chloride solution. The mixture was stirred at room temperature for a further 4 hours. Thereafter, 100 ml of dichloromethane was added and the mixture was washed with aqueous 2M hydrochloric acid. The organic phase was dried and concentrated to dryness. 773 mg of methyl 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoate was obtained.

¹H-NMR (400 MHz, DMSO-d₆): δ=8.68 (t, 1H); 7.77 (d, 1H); 7.69 (d, 1H); 3.87 (s, 3H); 3.28 (m, 2H); 1.12 (t, 3H).

Step 3: Preparation of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic Acid

To 773 mg (2.41 mmol) of methyl 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoate in 80 ml of methanol was added, at room temperature, 192 mg (4.82 mmol) of aqueous 1M sodium hydroxide solution. The mixture was stirred at 50° C. for 12 hours and then concentrated to dryness. The residue was taken up in a little water, and the solution was acidified by means of aqueous 2M hydrochloric acid and extracted with dichloromethane. The organic phase was dried and concentrated. 582 g of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic acid was obtained.

¹H-NMR (400 MHz, DMSO-d₆): δ=13.69 (br s, 1H); 8.65 (t, 1H); 7.72 (d, 1H); 7.66 (d, 1H); 3.26 (m, 2H); 1.12 (t, 3H).

Step 4: Preparation of 4-bromo-2-chloro-N³-ethyl-N¹-(1-methyl-1H-tetrazol-5-yl)isophthalamide

To an initial charge of 189 mg (0.61 mmol) of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic acid and 93.5 mg (0.92 mmol) of 5-amino-1-methyl-1H-tetrazole in 3 ml of pyridine was added, at room temperature, 155 mg (1.22 mmol) of oxalyl chloride. The mixture was stirred for a further 12 hours. Addition of 10 ml of water was followed by extraction with dichloromethane, and drying and concentration of the organic phases. The residue was purified by column chromatography (HPLC, C18, gradient: acetonitrile/water (++0.05% trifluoroacetic acid), 10/90→100/0 in 30 min). 66 mg of 4-bromo-2-chloro-N³-ethyl-N¹-(1-methyl-1H-tetrazol-5-yl)isophthalamide was obtained (Example No. 1-178).

The examples listed in the tables below were prepared analogously to the methods mentioned above or can be obtained analogously to the methods mentioned above. These compounds are very particularly preferred.

The abbreviations used here mean:

-   -   Me=methyl Bu=butyl Et=ethyl Pr=propyl c=cyclo Ph=phenyl

TABLE 1 Inventive compounds of the general formula (I) in which Q is Q¹ and R^(x) is methyl, and the other substituents have the definitions given below.

No. X Y Z 1-1 Me F Me 1-2 Me F Et 1-3 Me F c-Pr 1-4 Me Cl Me 1-5 Me Cl Et 1-6 Me Cl c-Pr 1-7 Me Br Me 1-8 Me Br Et 1-9 Me Br c-Pr 1-10 Me I Me 1-11 Me I Et 1-12 Me I c-Pr 1-13 Me SMe Me 1-14 Me SMe Et 1-15 Me SMe c-Pr 1-16 Me S(O)Me Me 1-17 Me S(O)Me Et 1-18 Me S(O)Me c-Pr 1-19 Me SO₂Me Me 1-20 Me SO₂Me Et 1-21 Me SO₂Me c-Pr 1-22 Me SO₂Me CH₂-c-Pr 1-23 Me SO₂Me CH₂CF₃ 1-24 Me SO₂Me CH₂CHF₂ 1-25 Me CF₃ Me 1-26 Me CF₃ Et 1-27 Me CF₃ c-Pr 1-28 Me CF₃ CH₂-c-Pr 1-29 Me CF₃ CH₂CF₃ 1-30 Me CF₃ CH₂CHF₂ 1-31 Me CF₃ CH(Me)-c-Pr 1-32 Me CF₃ Pr 1-33 Me CF₃ i-Pr 1-34 Me CF₃ CH₂CH₂OMe 1-35 Me CF₃ CH₂CH₂SMe 1-36 Me CF₃ CH₂CN 1-37 Me CF₃ CH₂-(tetrahydrofuran-2-yl) 1-38 Me CF₃ CH₂C(O)NMe₂ 1-39 Me CF₃ Ph 1-40 Me CF₃ CH₂-(thien-2-yl) 1-41 Me CF₃ Oxetan-3-yl 1-42 Me CF₃ c-Bu 1-43 Me CF₃ c-Pentyl 1-44 Me CHF₂ Me 1-45 Me CHF₂ Et 1-46 Me CHF₂ c-Pr 1-47 Me CHF₂ CH₂-c-Pr 1-48 Me CHF₂ CH₂CF₃ 1-49 Me CHF₂ CH₂CHF₂ 1-50 Me C₂F₅ Me 1-51 Me C₂F₅ Et 1-52 Me C₂F₅ c-Pr 1-53 OMe Cl Me 1-54 OMe Cl Et 1-55 OMe Cl c-Pr 1-56 OMe CF₃ Me 1-57 OMe CF₃ Et 1-58 OMe CF₃ c-Pr 1-59 OMe CF₃ CH₂-c-Pr 1-60 OMe CF₃ CH₂CF₃ 1-71 OMe CF₃ CH₂CHF₂ 1-72 OMe CHF₂ Me 1-73 OMe CHF₂ Et 1-74 OMe CHF₂ c-Pr 1-75 OMe CHF₂ CH-c-Pr 1-76 OMe CHF₂ CH₂CF₃ 1-77 OMe CHF₂ CH₂CHF₂ 1-78 SMe SO₂Me Me 1-79 SMe SO₂Me Et 1-80 SMe SO₂Me c-Pr 1-81 SMe CF₃ Me 1-82 SMe CF₃ Et 1-83 SMe CF₃ c-Pr 1-84 SMe CF₃ CH₂-c-Pr 1-85 SMe CF₃ CH₂CF₃ 1-86 SMe CF₃ CH₂CHF₂ 1-87 SMe CHF₂ Me 1-88 SMe CHF₂ Et 1-89 SMe CHF₂ c-Pr 1-90 SMe CHF₂ CH₂-c-Pr 1-91 SMe CHF₂ CH₂CF₃ 1-92 SMe CHF₂ CH₂CHF₂ 1-93 SEt CF₃ Me 1-94 SEt CF₃ Et 1-95 SEt CF₃ c-Pr 1-96 SEt CF₃ CH₂-c-Pr 1-97 SEt CF₃ CH₂CF₃ 1-98 SEt CF₃ CH₂CHF₂ 1-99 SEt CHF₂ Me 1-100 SEt CHF₂ Et 1-101 SEt CHF₂ c-Pr 1-102 SEt CHF₂ CH₂-c-Pr 1-103 SEt CHF₂ CH₂CF₃ 1-104 SEt CHF₂ CH₂CHF₂ 1-105 F CF₃ Me 1-106 F CF₃ Et 1-107 F CF₃ c-Pr 1-108 F CF₃ CH₂-c-Pr 1-109 F CF₃ CH₂CF₃ 1-110 F CF₃ CH₂CHF₂ 1-111 F CHF₂ Me 1-112 F CHF₂ Et 1-113 F CHF₂ c-Pr 1-114 F CHF₂ CH₂-c-Pr 1-115 F CHF₂ CH₂CF₃ 1-116 F CHF₂ CH₂CHF₂ 1-117 Cl SMe Me 1-118 Cl SMe Et 1-119 Cl SMe c-Pr 1-120 Cl S(O)Me Me 1-121 Cl S(O)Me Et 1-122 Cl S(O)Me c-Pr 1-123 Cl SO₂Me Me 1-124 Cl SO₂Me Et 1-125 Cl SO₂Me c-Pr 1-126 Cl SO₂Me CH₂-c-Pr 1-127 Cl SO₂Me CH₂CF₃ 1-128 Cl SO₂Me CH₂CHF₂ 1-129 Cl CF₃ Me 1-130 Cl CF₃ Et 1-131 Cl CF₃ c-Pr 1-132 Cl CF₃ CH₂-c-Pr 1-133 Cl CF₃ CH₂CF₃ 1-134 Cl CF₃ CH₂CHF₂ 1-135 Cl CF₃ CH(Me)-c-Pr 1-136 Cl CF₃ Pr 1-137 Cl CF₃ iPr 1-138 Cl CF₃ CH₂CH₂OMe 1-139 Cl CF₃ CH₂CH₂SMe 1-140 Cl CF₃ CH₂CN 1-141 Cl CF₃ CH₂-(tetrahydrofuran-2-yl) 1-142 Cl CF₃ CH₂C(O)NMe₂ 1-143 Cl CF₃ Ph 1-144 Cl CF₃ CH₂-(thien-2-yl) 1-145 Cl CF₃ Oxetan-3-yl 1-146 Cl CF₃ cBu 1-147 Cl CHF₂ Me 1-148 Cl CHF₂ Et 1-149 Cl CHF₂ c-Pr 1-150 Cl CHF₂ CH₂-c-Pr 1-151 Cl CHF₂ CH₂CF₃ 1-152 Cl CHF₂ CH₂CHF₂ 1-153 Cl CHF₂ CH(Me)-c-Pr 1-154 Cl CHF₂ Pr 1-155 Cl CHF₂ iPr 1-156 Cl CHF₂ CH₂CH₂OMe 1-157 Cl CHF₂ CH₂CH₂SMe 1-158 Cl CHF₂ CH₂CN 1-159 Cl CHF₂ CH₂-(tetrahydrofuran-2-yl) 1-160 Cl CHF₂ CH₂C(O)NMe₂ 1-161 Cl CHF₂ Ph 1-162 Cl CHF₂ CH₂-(thien-2-yl) 1-163 Cl CHF₂ Oxetan-3-yl 1-164 Cl CHF₂ cBu 1-165 Cl C₂F₅ Me 1-166 Cl C₂F₅ Et 1-167 Cl C₂F₅ c-Pr 1-168 Cl C₂F₅ CH₂-c-Pr 1-169 Cl C₂F₅ CH₂CF₃ 1-170 Cl C₂F₅ CH₂CHF₂ 1-171 Cl Cl Me 1-172 Cl Cl Et 1-173 Cl Cl c-Pr 1-174 Cl Cl CH₂-c-Pr 1-175 Cl Cl CH₂CF₃ 1-176 Cl Cl CH₂CHF₂ 1-177 Cl Br Me 1-178 Cl Br Et 1-179 Cl Br c-Pr 1-180 Cl Br CH₂-c-Pr 1-181 Cl Br CH₂CF₃ 1-182 Cl Br CH₂CHF₂ 1-183 Cl Br CH(Me)-c-Pr 1-184 Cl Br Pr 1-185 Cl Br i-Pr 1-186 Cl Br CH₂CH₂OMe 1-187 Cl Br CH₂CH₂SMe 1-188 Cl Br CH₂CN 1-189 Cl Br CH₂-(tetrahydrofuran-2-yl) 1-190 Cl Br CH₂C(O)NMe₂ 1-191 Cl Br Ph 1-192 Cl Br CH₂-(thien-2-yl) 1-193 Cl Br Oxetan-3-yl 1-194 Cl Br cBu 1-195 Cl I Me 1-196 Cl I Et 1-197 Cl I c-Pr 1-198 Cl I CH₂-c-Pr 1-199 Cl I CH₂CF₃ 1-200 Cl I CH₂CHF₂ 1-201 Br SO₂Me Me 1-202 Br SO₂Me Et 1-203 Br SO₂Me c-Pr 1-204 Br SO₂Me CH₂-c-Pr 1-205 Br SO₂Me CH₂CF₃ 1-206 Br SO₂Me CH₂CHF₂ 1-207 Br CF₃ Me 1-208 Br CF₃ Et 1-209 Br CF₃ c-Pr 1-210 Br CF₃ CH₂-c-Pr 1-211 Br CF₃ CH₂CF₃ 1-212 Br CF₃ CH₂CHF₂ 1-213 Br CF₃ CH(Me)-c-Pr 1-214 Br CF₃ Pr 1-215 Br CF₃ i-Pr 1-216 Br CF₃ CH₂CH₂OMe 1-217 Br CF₃ CH₂CH₂SMe 1-218 Br CF₃ CH₂CN 1-219 Br CF₃ CH₂-(tetrahydrofuran-2-yl) 1-220 Br CF₃ CH₂C(O)NMe₂ 1-221 Br CF₃ Ph 1-222 Br CF₃ CH₂-(thien-2-yl) 1-223 Br CF₃ Oxetan-3-yl 1-224 Br CF₃ c-Bu 1-225 Br CHF₂ Me 1-226 Br CHF₂ Et 1-227 Br CHF₂ c-Pr 1-228 Br CHF₂ CH₂-c-Pr 1-229 Br CHF₂ CH₂CF₃ 1-230 Br CHF₂ CH₂CHF₂ 1-231 Br C₂F₅ Me 1-232 Br C₂F₅ Et 1-233 Br C₂F₅ c-Pr 1-234 Br C₂F₅ CH₂-c-Pr 1-235 Br C₂F₅ CH₂CF₃ 1-236 Br C₂F₅ CH₂CHF₂ 1-237 I SO₂Me Me 1-238 I SO₂Me Et 1-239 I SO₂Me c-Pr 1-240 I CF₃ Me 1-241 I CF₃ Et 1-242 I CF₃ c-Pr 1-243 I CF₃ CH₂-c-Pr 1-244 I CF₃ CH₂CF₃ 1-245 I CF₃ CH₂CHF₂ 1-246 I CHF₂ Me 1-247 I CHF₂ Et 1-248 I CHF₂ c-Pr 1-249 I CHF₂ CH₂-c-Pr 1-250 I CHF₂ CH₂CF₃ 1-251 I CHF₂ CH₂CHF₂ 1-252 I C₂F₅ Me 1-253 I C₂F₅ Et 1-254 I C₂F₅ c-Pr 1-255 CH₂OMe CF₃ Me 1-256 CH₂OMe CF₃ Et 1-257 CH₂OMe CF₃ c-Pr 1-258 CH₂OMe CF₃ CH₂-c-Pr 1-259 CH₂OMe CF₃ CH₂CF₃ 1-260 CH₂OMe CF₃ CH₂CHF₂ 1-261 CH₂OMe CHF₂ Me 1-262 CH₂OMe CHF₂ Et 1-263 CH₂OMe CHF₂ c-Pr 1-264 CH₂OMe CHF₂ CH₂-c-Pr 1-265 CH₂OMe CHF₂ CH₂CF₃ 1-266 CH₂OMe CHF₂ CH₂CHF₂ 1-267 CH₂OMe CHF₂ c-Pentyl 1-268 CH₂OMe SO₂Me Me 1-269 CH₂OMe SO₂Me Et 1-270 CH₂OMe SO₂Me c-Pr 1-271 Et CF₃ Me 1-272 Et CF₃ Et 1-273 Et CF₃ c-Pr 1-274 Et CF₃ CH₂-c-Pr 1-275 Et CF₃ CH₂cF₃ 1-276 Et CF₃ CH₂CHF₂ 1-277 Et CHF₂ Me 1-278 Et CHF₂ Et 1-279 Et CHF₂ c-Pr 1-280 Et CHF₂ CH₂-c-Pr 1-281 Et CHF₂ CH₂cF₃ 1-282 Et CHF₂ CH₂CHF₂ 1-283 Et C₂F₅ Me 1-284 Et C₂F₅ Et 1-285 Et C₂F₅ c-Pr 1-286 c-Pr CF₃ Me 1-287 c-Pr CF₃ Et 1-288 c-Pr CF₃ c-Pr 1-289 c-Pr CF₃ CH₂-c-Pr 1-290 c-Pr CF₃ CH₂CF₃ 1-291 c-Pr CF₃ CH₂CHF₂ 1-292 c-Pr CF₃ CH(Me)-c-Pr 1-293 c-Pr CF₃ Pr 1-294 c-Pr CF₃ iPr 1-295 c-Pr CF₃ CH₂CH₂OMe 1-296 c-Pr CF₃ CH₂CH₂SMe 1-297 c-Pr CF₃ CH₂CN 1-298 c-Pr CF₃ CH₂-(tetrahydrofuran-2-yl) 1-299 c-Pr CF₃ CH₂C(O)NMe₂ 1-300 c-Pr CF₃ Ph 1-301 c-Pr CF₃ CH₂-(thien-2-yl) 1-302 c-Pr CF₃ Oxetan-3-yl 1-303 c-Pr CF₃ c-Bu 1-304 c-Pr CHF₂ Me 1-305 c-Pr CHF₂ Et 1-306 c-Pr CHF₂ c-Pr 1-307 c-Pr CHF₂ CH₂-c-Pr 1-308 c-Pr CHF₂ CH₂CF₃ 1-309 c-Pr CHF₂ CH₂CHF₂ 1-310 c-Pr CHF₂ CH(Me)-c-Pr 1-311 c-Pr CHF₂ Pr 1-312 c-Pr CHF₂ i-Pr 1-313 c-Pr CHF₂ CH₂CH₂OMe 1-314 c-Pr CHF₂ CH₂CH₂SMe 1-315 c-Pr CHF₂ CH₂CN 1-316 c-Pr CHF₂ CH₂-(tetrahydrofuran-2-yl) 1-317 c-Pr CHF₂ CH₂C(O)NMe₂ 1-318 c-Pr CHF₂ Ph 1-319 c-Pr CHF₂ CH₂-(thien-2-yl) 1-320 c-Pr CHF₂ Oxetan-3-yl 1-321 c-Pr CHF₂ cBu 1-322 c-Pr C₂F₅ Me 1-323 c-Pr C₂F₅ Et 1-324 c-Pr C₂F₅ c-Pr 1-325 c-Pr C₂F₅ CH₂-c-Pr 1-326 c-Pr C₂F₅ CH₂CF₃ 1-327 c-Pr C₂F₅ CH₂CHF₂ 1-328 c-Pr SO₂Me Me 1-329 c-Pr SO₂Me Et 1-330 c-Pr SO₂Me c-Pr 1-331 CF₃ CF₃ Me 1-332 CF₃ CF₃ Et 1-333 CF₃ CF₃ c-Pr 1-334 CF₃ CF₃ CH₂-c-Pr 1-335 CF₃ CF₃ CH₂CF₃ 1-336 CF₃ CF₃ CH₂CHF₂ 1-337 Cl CF₃ Acetyl 1-338 Cl CF₃ H 1-339 Me CHF₂ CH(Me)-c-Pr 1-340 Br CHF₂ CH(Me)-c-Pr 1-341 Et CF₃ CH(Me)-c-Pr 1-342 Br Br Me 1-343 Br Br Et 1-344 Br Br c-Pr 1-345 Me CHF₂ Pr 1-346 Me CHF₂ i-Pr 1-347 Me CHF₂ CH₂CH₂OMe 1-348 Me CHF₂ CH₂CH₂SMe 1-349 Br Cl Me 1-350 Br Cl Et 1-351 Br Cl c-Pr 1-352 SMe CF₃ CH(Me)-c-Pr 1-353 SMe CHF₂ CH(Me)-c-Pr 1-354 Cl OMe Me 1-355 Cl OMe Et 1-356 Cl OMe c-Pr 1-357 Cl CF₃ OMe 1-358 Cl CF₃ OEt 1-359 Cl CF₃ OPr 1-360 Cl CF₃ Oi-Pr 1-361 Cl CHF₂ OMe 1-362 Cl CHF₂ OEt 1-363 Cl CHF₂ OPr 1-364 Cl CHF₂ Oi-Pr

TABLE 2 Inventive compounds of the general formula (I) in which Q is Q¹ and R^(x) is ethyl, and the other substituents have the definitions given below.

No. X Y Z 2-1 Me F Me 2-2 Me F Et 2-3 Me F c-Pr 2-4 Me Cl Me 2-5 Me Cl Et 2-6 Me Cl c-Pr 2-7 Me Br Me 2-8 Me Br Et 2-9 Me Br c-Pr 2-10 Me I Me 2-11 Me I Et 2-12 Me I c-Pr 2-13 Me SMe Me 2-14 Me SMe Et 2-15 Me SMe c-Pr 2-16 Me S(O)Me Me 2-17 Me S(O)Me Et 2-18 Me S(O)Me c-Pr 2-19 Me SO₂Me Me 2-20 Me SO₂Me Et 2-21 Me SO₂Me c-Pr 2-22 Me SO₂Me CH₂-c-Pr 2-23 Me SO₂Me CH₂CF₃ 2-24 Me SO₂Me CH₂CHF₂ 2-25 Me CF₃ Me 2-26 Me CF₃ Et 2-27 Me CF₃ c-Pr 2-28 Me CF₃ CH₂-c-Pr 2-29 Me CF₃ CH₂CF₃ 2-30 Me CF₃ CH₂CHF₂ 2-31 Me CF₃ CH(Me)-c-Pr 2-32 Me CF₃ Pr 2-33 Me CF₃ i-Pr 2-34 Me CF₃ CH₂CH₂OMe 2-35 Me CF₃ CH₂CH₂SMe 2-36 Me CF₃ CHCN 2-37 Me CF₃ CH₂-(tetrahydrofuran-2-yl) 2-38 Me CF₃ CH₂C(O)NMe₂ 2-39 Me CF₃ Ph 2-40 Me CF₃ CH₂-(thien-2-yl) 2-41 Me CF₃ Oxetan-3-yl 2-42 Me CF₃ c-Bu 2-43 Me CF₃ c-Pentyl 2-44 Me CHF₂ Me 2-45 Me CHF₂ Et 2-46 Me CHF₂ c-Pr 2-47 Me CHF₂ CH₂-c-Pr 2-48 Me CHF₂ CH₂CF₃ 2-49 Me CHF₂ CH₂CHF₂ 2-50 Me C₂F₅ Me 2-51 Me C₂F₅ Et 2-52 Me C₂F₅ c-Pr 2-53 OMe Cl Me 2-54 OMe Cl Et 2-55 OMe Cl c-Pr 2-56 OMe CF₃ Me 2-57 OMe CF₃ Et 2-58 OMe CF₃ c-Pr 2-59 OMe CF₃ CH₂-c-Pr 2-60 OMe CF₃ CH₂CF₃ 2-71 OMe CF₃ CH₂CHF₂ 2-72 OMe CHF₂ Me 2-73 OMe CHF₂ Et 2-74 OMe CHF₂ c-Pr 2-75 OMe CHF₂ CH₂-c-Pr 2-76 OMe CHF₂ CH₂CF₃ 2-77 OMe CHF₂ CH₂CHF₂ 2-78 SMe SO₂Me Me 2-79 SMe SO₂Me Et 2-80 SMe SO₂Me c-Pr 2-81 SMe CF₃ Me 2-82 SMe CF₃ Et 2-83 SMe CF₃ c-Pr 2-84 SMe CF₃ CH₂-c-Pr 2-85 SMe CF₃ CH₂CF₃ 2-86 SMe CF₃ CH₂CHF₂ 2-87 SMe CHF₂ Me 2-88 SMe CHF₂ Et 2-89 SMe CHF₂ c-Pr 2-90 SMe CHF₂ CH₂-c-Pr 2-91 SMe CHF₂ CH₂CF₃ 2-92 SMe CHF₂ CH₂CHF₂ 2-93 SEt CF₃ Me 2-94 SEt CF₃ Et 2-95 SEt CF₃ c-Pr 2-96 SEt CF₃ CH₂-c-Pr 2-97 SEt CF₃ CH₂CF₃ 2-98 SEt CF₃ CH₂CHF₂ 2-99 SEt CHF₂ Me 2-100 SEt CHF₂ Et 2-101 SEt CHF₂ c-Pr 2-102 SEt CHF₂ CH₂-c-Pr 2-103 SEt CHF₂ CH₂CF₃ 2-104 SEt CHF₂ CH₂CHF₂ 2-105 F CF₃ Me 2-106 F CF₃ Et 2-107 F CF₃ c-Pr 2-108 F CF₃ CH₂-c-Pr 2-109 F CF₃ CH₂CF₃ 2-110 F CF₃ CH₂CHF₂ 2-111 F CHF₂ Me 2-112 F CHF₂ Et 2-113 F CHF₂ c-Pr 2-114 F CHF₂ CH₂-c-Pr 2-115 F CHF₂ CH₂CF₃ 2-116 F CHF₂ CH₂CHF₂ 2-117 Cl SMe Me 2-118 Cl SMe Et 2-119 Cl SMe c-Pr 2-120 Cl S(O)Me Me 2-121 Cl S(O)Me Et 2-122 Cl S(O)Me c-Pr 2-123 Cl SO₂Me Me 2-124 Cl SO₂Me Et 2-125 Cl SO₂Me c-Pr 2-126 Cl SO₂Me CH₂-c-Pr 2-127 Cl SO₂Me CH₂CF₃ 2-128 Cl SO₂Me CH₂CHF₂ 2-129 Cl CF₃ Me 2-130 Cl CF₃ Et 2-131 Cl CF₃ c-Pr 2-132 Cl CF₃ CH₂-c-Pr 2-133 Cl CF₃ CH₂cF₃ 2-134 Cl CF₃ CH₂CHF₂ 2-135 Cl CF₃ CH(Me)-c-Pr 2-136 Cl CF₃ Pr 2-137 Cl CF₃ i-Pr 2-138 Cl CF₃ CH₂CH₂OMe 2-139 Cl CF₃ CH₂CH₂SMe 2-140 Cl CF₃ CH₂CN 2-141 Cl CF₃ CH₂-(tetrahydrofuran-2-yl) 2-142 Cl CF₃ CH₂C(O)NMe₂ 2-143 Cl CF₃ Ph 2-144 Cl CF₃ CH₂-(thien-2-yl) 2-145 Cl CF₃ Oxetan-3-yl 2-146 Cl CF₃ c-Bu 2-147 Cl CHF₂ Me 2-148 Cl CHF₂ Et 2-149 Cl CHF₂ c-Pr 2-150 Cl CHF₂ CH₂-c-Pr 2-151 Cl CHF₂ CH₂CF₃ 2-152 Cl CHF₂ CH₂CHF₂ 2-153 Cl CHF₂ CH(Me)-c-Pr 2-154 Cl CHF₂ Pr 2-155 Cl CHF₂ i-Pr 2-156 Cl CHF₂ CH₂CH₂OMe 2-157 Cl CHF₂ CH₂CH₂SMe 2-158 Cl CHF₂ CH₂CN 2-159 Cl CHF₂ CH₂-(tetrahydrofuran-2-yl) 2-160 Cl CHF₂ CH₂C(O)NMe₂ 2-161 Cl CHF₂ Ph 2-162 Cl CHF₂ CH₂-(thien-2-yl) 2-163 Cl CHF₂ Oxetan-3-yl 2-164 Cl CHF₂ c-Bu 2-165 Cl C₂F₅ Me 2-166 Cl C₂F₅ Et 2-167 Cl C₂F₅ c-Pr 2-168 Cl C₂F₅ CH₂-c-Pr 2-169 Cl C₂F₅ CH₂CF₃ 2-170 Cl C₂F₅ CH₂CHF₂ 2-171 Cl Cl Me 2-172 Cl Cl Et 2-173 Cl Cl c-Pr 2-174 Cl Cl CH-c-Pr 2-175 Cl Cl CH₂CF₃ 2-176 Cl Cl CH₂CHF₂ 2-177 Cl Br Me 2-178 Cl Br Et 2-179 Cl Br c-Pr 2-180 Cl Br CH-c-Pr 2-181 Cl Br CH₂CF₃ 2-182 Cl Br CH₂CHF₂ 2-183 Cl Br CH(Me)-c-Pr 2-184 Cl Br Pr 2-185 Cl Br i-Pr 2-186 Cl Br CH₂CH₂OMe 2-187 Cl Br CH₂CH₂SMe 2-188 Cl Br CH₂CN 2-189 Cl Br CH₂-(tetrahydrofuran-2-yl) 2-190 Cl Br CH₂C(O)NMe₂ 2-191 Cl Br Ph 2-192 Cl Br CH₂-(thien-2-yl) 2-193 Cl Br Oxetan-3-yl 2-194 Cl Br c-Bu 2-195 Cl I Me 2-196 Cl I Et 2-197 Cl I c-Pr 2-198 Cl I CH₂-c-Pr 2-199 Cl I CH₂CF₃ 2-200 Cl I CH₂CHF₂ 2-201 Br SO₂Me Me 2-202 Br SO₂Me Et 2-203 Br SO₂Me c-Pr 2-204 Br SO₂Me CH₂-c-Pr 2-205 Br SO₂Me CH₂CF₃ 2-206 Br SO₂Me CH₂CHF₂ 2-207 Br CF₃ Me 2-208 Br CF₃ Et 2-209 Br CF₃ c-Pr 2-210 Br CF₃ CH₂-c-Pr 2-211 Br CF₃ CH₂CF₃ 2-212 Br CF₃ CH₂CHF₂ 2-213 Br CF₃ CH(Me)-c-Pr 2-214 Br CF₃ Pr 2-215 Br CF₃ i-Pr 2-216 Br CF₃ CH₂CH₂OMe 2-217 Br CF₃ CH₂CH₂SMe 2-218 Br CF₃ CH₂CN 2-219 Br CF₃ CH₂-(tetrahydrofuran-2-yl) 2-220 Br CF₃ CH₂C(O)NMe₂ 2-221 Br CF₃ Ph 2-222 Br CF₃ CH₂-(thien-2-yl) 2-223 Br CF₃ Oxetan-3-yl 2-224 Br CF₃ c-Bu 2-225 Br CHF₂ Me 2-226 Br CHF₂ Et 2-227 Br CHF₂ c-Pr 2-228 Br CHF₂ CH₂-c-Pr 2-229 Br CHF₂ CH₂CF₃ 2-230 Br CHF₂ CH₂CHF₂ 2-231 Br C₂F₅ Me 2-232 Br C₂F₅ Et 2-233 Br C₂F₅ c-Pr 2-234 Br C₂F₅ CH₂-c-Pr 2-235 Br C₂F₅ CH₂CF₃ 2-236 Br C₂F₅ CH₂CHF₂ 2-237 I SO₂Me Me 2-238 I SO₂Me Et 2-239 I SO₂Me c-Pr 2-240 I CF₃ Me 2-241 I CF₃ Et 2-242 I CF₃ c-Pr 2-243 I CF₃ CH₂-c-Pr 2-244 I CF₃ CH₂CF₃ 2-245 I CF₃ CH₂CHF₂ 2-246 I CHF₂ Me 2-247 I CHF₂ Et 2-248 I CHF₂ c-Pr 2-249 I CHF₂ CH₂-c-Pr 2-250 I CHF₂ CH₂CF₃ 2-251 I CHF₂ CH₂CHF₂ 2-252 I C₂F₅ Me 2-253 I C₂F₅ Et 2-254 I C₂F₅ c-Pr 2-255 CH₂OMe CF₃ Me 2-256 CH₂OMe CF₃ Et 2-257 CH₂OMe CF₃ c-Pr 2-258 CH₂OMe CF₃ CH₂-c-Pr 2-259 CH₂OMe CF₃ CH₂CF₃ 2-260 CH₂OMe CF₃ CH₂CHF₂ 2-261 CH₂OMe CHF₂ Me 2-262 CH₂OMe CHF₂ Et 2-263 CH₂OMe CHF₂ c-Pr 2-264 CH₂OMe CHF₂ CH₂-c-Pr 2-265 CH₂OMe CHF₂ CH₂CF₃ 2-266 CH₂OMe CHF₂ CH₂CHF₂ 2-267 CH₂OMe CHF₂ c-Pentyl 2-268 CH₂OMe SO₂Me Me 2-269 CH₂OMe SO₂Me Et 2-270 CH₂OMe SO₂Me c-Pr 2-271 Et CF₃ Me 2-272 Et CF₃ Et 2-273 Et CF₃ c-Pr 2-274 Et CF₃ CH₂-c-Pr 2-275 Et CF₃ CH₂CF₃ 2-276 Et CF₃ CH₂CHF₂ 2-277 Et CHF₂ Me 2-278 Et CHF₂ Et 2-279 Et CHF₂ c-Pr 2-280 Et CHF₂ CH₂-c-Pr 2-281 Et CHF₂ CH₂CF₃ 2-282 Et CHF₂ CH₂CHF₂ 2-283 Et C₂F₅ Me 2-284 Et C₂F₅ Et 2-285 Et C₂F₅ c-Pr 2-286 c-Pr CF₃ Me 2-287 c-Pr CF₃ Et 2-288 c-Pr CF₃ c-Pr 2-289 c-Pr CF₃ CH₂-c-Pr 2-290 c-Pr CF₃ CH₂CF₃ 2-291 c-Pr CF₃ CH₂CHF₂ 2-292 c-Pr CF₃ CH(Me)-c-Pr 2-293 c-Pr CF₃ Pr 2-294 c-Pr CF₃ i-Pr 2-295 c-Pr CF₃ CH₂CH₂OMe 2-296 c-Pr CF₃ CH₂CH₂SMe 2-297 c-Pr CF₃ CH₂CN 2-298 c-Pr CF₃ CH₂-(tetrahydrofuran-2-yl) 2-299 c-Pr CF₃ CH₂C(O)NMe₂ 2-300 c-Pr CF₃ Ph 2-301 c-Pr CF₃ CH₂-(thien-2-yl) 2-302 c-Pr CF₃ Oxetan-3-yl 2-303 c-Pr CF₃ c-Bu 2-304 c-Pr CHF₂ Me 2-305 c-Pr CHF₂ Et 2-306 c-Pr CHF₂ c-Pr 2-307 c-Pr CHF₂ CH₂-c-Pr 2-308 c-Pr CHF₂ CH₂CF₃ 2-309 c-Pr CHF₂ CH₂CHF₂ 2-310 c-Pr CHF₂ CH(Me)-c-Pr 2-311 c-Pr CHF₂ Pr 2-312 c-Pr CHF₂ i-Pr 2-313 c-Pr CHF₂ CH₂CH₂OMe 2-314 c-Pr CHF₂ CH₂CH₂SMe 2-315 c-Pr CHF₂ CH₂CN 2-316 c-Pr CHF₂ CH₂-(tetrahydrofuran-2-yl) 2-317 c-Pr CHF₂ CH₂C(O)NMe₂ 2-318 c-Pr CHF₂ Ph 2-319 c-Pr CHF₂ CH₂-(thien-2-yl) 2-320 c-Pr CHF₂ Oxetan-3-yl 2-321 c-Pr CHF₂ c-Bu 2-322 c-Pr C₂F₅ Me 2-323 c-Pr C₂F₅ Et 2-324 c-Pr C₂F₅ c-Pr 2-325 c-Pr C₂F₅ CH₂-c-Pr 2-326 c-Pr C₂F₅ CH₂CF₃ 2-327 c-Pr C₂F₅ CH₂CHF₂ 2-328 c-Pr SO₂Me Me 2-329 c-Pr SO₂Me Et 2-330 c-Pr SO₂Me c-Pr 2-331 CF₃ CF₃ Me 2-332 CF₃ CF₃ Et 2-333 CF₃ CF₃ c-Pr 2-334 CF₃ CF₃ CH₂-c-Pr 2-335 CF₃ CF₃ CH₂CF₃ 2-336 CF₃ CF₃ CH₂CHF₂ 2-337 Cl CF₃ Acetyl 2-338 Cl CF₃ H 2-339 Me CHF₂ CH(Me)-c-Pr 2-340 Br CHF₂ CH(Me)-c-Pr 2-341 Et CF₃ CH(Me)-c-Pr 2-342 Br Br Et 2-343 Br Br c-Pr 2-344 Me CHF₂ Pr 2-345 Me CHF₂ i-Pr 2-346 Me CHF₂ CH₂CH₂OMe 2-347 Me CHF₂ CH₂CH₂SMe 2-348 Br Cl Et 2-349 Br Cl c-Pr 2-350 SMe CF₃ CH(Me)-c-Pr 2-351 SMe CHF₂ CH(Me)-c-Pr 2-352 Cl OMe Me 2-353 Cl OMe Et 2-354 Cl OMe c-Pr 2-355 Br Br Me 2-356 Br Cl Me 2-357 Cl CF₃ OMe 2-358 Cl CF₃ OEt 2-359 Cl CF₃ OPr 2-360 Cl CF₃ Oi-Pr 2-361 Cl CHF₂ OMe 2-362 Cl CHF₂ OEt 2-363 Cl CHF₂ OPr 2-364 Cl CHF₂ Oi-Pr

TABLE 3 Inventive compounds of the general formula (I) in which Q is Q¹ and R^(x) is propyl, and the other substituents have the definitions given below.

No. X Y Z 3-1 Me F Me 3-2 Me F Et 3-3 Me F c-Pr 3-4 Me Cl Me 3-5 Me Cl Et 3-6 Me Cl c-Pr 3-7 Me Br Me 3-8 Me Br Et 3-9 Me Br c-Pr 3-10 Me I Me 3-11 Me I Et 3-12 Me I c-Pr 3-13 Me SMe Me 3-14 Me SMe Et 3-15 Me SMe c-Pr 3-16 Me S(O)Me Me 3-17 Me S(O)Me Et 3-18 Me S(O)Me c-Pr 3-19 Me SO₂Me Me 3-20 Me SO₂Me Et 3-21 Me SO₂Me c-Pr 3-22 Me SO₂Me CH₂-c-Pr 3-23 Me SO₂Me CH₂CF₃ 3-24 Me SO₂Me CH₂CHF₂ 3-25 Me CF₃ Me 3-26 Me CF₃ Et 3-27 Me CF₃ c-Pr 3-28 Me CF₃ CH₂-c-Pr 3-29 Me CF₃ CH₂CF₃ 3-30 Me CF₃ CH₂CHF₂ 3-31 Me CF₃ CH(Me)-c-Pr 3-32 Me CF₃ Pr 3-33 Me CF₃ i-Pr 3-34 Me CF₃ CH₂CH₂OMe 3-35 Me CF₃ CH₂CH₂SMe 3-36 Me CF₃ CH₂CN 3-37 Me CF₃ CH₂-(tetrahydrofuran-2-yl) 3-38 Me CF₃ CH₂C(O)NMe₂ 3-39 Me CF₃ Ph 3-40 Me CF₃ CH₂-(thien-2-yl) 3-41 Me CF₃ Oxetan-3-yl 3-42 Me CF₃ c-Bu 3-43 Me CF₃ c-Pentyl 3-44 Me CHF₂ Me 3-45 Me CHF₂ Et 3-46 Me CHF₂ c-Pr 3-47 Me CHF₂ CH₂-c-Pr 3-48 Me CHF₂ CH₂CF₃ 3-49 Me CHF₂ CH₂CHF₂ 3-50 Me C₂F₅ Me 3-51 Me C₂F₅ Et 3-52 Me C₂F₅ c-Pr 3-53 OMe Cl Me 3-54 OMe Cl Et 3-55 OMe Cl c-Pr 3-56 OMe CF₃ Me 3-57 OMe CF₃ Et 3-58 OMe CF₃ c-Pr 3-59 OMe CF₃ CH₂-c-Pr 3-60 OMe CF₃ CH₂CF₃ 3-71 OMe CF₃ CH₂CHF₂ 3-72 OMe CHF₂ Me 3-73 OMe CHF₂ Et 3-74 OMe CHF₂ c-Pr 3-75 OMe CHF₂ CH₂-c-Pr 3-76 OMe CHF₂ CH₂CF₃ 3-77 OMe CHF₂ CH₂CHF₂ 3-78 SMe SO₂Me Me 3-79 SMe SO₂Me Et 3-80 SMe SO₂Me c-Pr 3-81 SMe CF₃ Me 3-82 SMe CF₃ Et 3-83 SMe CF₃ c-Pr 3-84 SMe CF₃ CH₂-c-Pr 3-85 SMe CF₃ CH₂CF₃ 3-86 SMe CF₃ CH₂CHF₂ 3-87 SMe CHF₂ Me 3-88 SMe CHF₂ Et 3-89 SMe CHF₂ c-Pr 3-90 SMe CHF₂ CH₂-c-Pr 3-91 SMe CHF₂ CH₂cF₃ 3-92 SMe CHF₂ CH₂CHF₂ 3-93 SEt CF₃ Me 3-94 SEt CF₃ Et 3-95 SEt CF₃ c-Pr 3-96 SEt CF₃ CH₂-c-Pr 3-97 SEt CF₃ CH₂CF₃ 3-98 SEt CF₃ CH₂CHF₂ 3-99 SEt CHF₂ Me 3-100 SEt CHF₂ Et 3-101 SEt CHF₂ c-Pr 3-102 SEt CHF₂ CH₂-c-Pr 3-103 SEt CHF₂ CH₂CF₃ 3-104 SEt CHF₂ CH₂CHF₂ 3-105 F CF₃ Me 3-106 F CF₃ Et 3-107 F CF₃ c-Pr 3-108 F CF₃ CH₂-c-Pr 3-109 F CF₃ CH₂CF₃ 3-110 F CF₃ CH₂CHF₂ 3-111 F CHF₂ Me 3-112 F CHF₂ Et 3-113 F CHF₂ c-Pr 3-114 F CHF₂ CH₂-c-Pr 3-115 F CHF₂ CH₂CF₃ 3-116 F CHF₂ CH₂CHF₂ 3-117 Cl SMe Me 3-118 Cl SMe Et 3-119 Cl SMe c-Pr 3-120 Cl S(O)Me Me 3-121 Cl S(O)Me Et 3-122 Cl S(O)Me c-Pr 3-123 Cl SO₂Me Me 3-124 Cl SO₂Me Et 3-125 Cl SO₂Me c-Pr 3-126 Cl SO,Me CH₂-c-Pr 3-127 Cl SO,Me CH₂cF₃ 3-128 Cl SO,Me CH₂CHF₂ 3-129 Cl CF₃ Me 3-130 Cl CF₃ Et 3-131 Cl CF₃ c-Pr 3-132 Cl CF₃ CH₂-c-Pr 3-133 Cl CF₃ CH₂cF₃ 3-134 Cl CF₃ CH₂CHF₂ 3-135 Cl CF₃ CH(Me)-c-Pr 3-136 Cl CF₃ Pr 3-137 Cl CF₃ i-Pr 3-138 Cl CF₃ CH₂CH₂OMe 3-139 Cl CF₃ CH₂CH₂SMe 3-140 Cl CF₃ CH₂CN 3-141 Cl CF₃ CH₂-(tetrahydrofuran-2-yl) 3-142 Cl CF₃ CH₂C(O)NMe₂ 3-143 Cl CF₃ Ph 3-144 Cl CF₃ CH₂-(thien-2-yl) 3-145 Cl CF₃ Oxetan-3-yl 3-146 Cl CF₃ c-Bu 3-147 Cl CHF₂ Me 3-148 Cl CHF₂ Et 3-149 Cl CHF₂ c-Pr 3-150 Cl CHF₂ CH₂-c-Pr 3-151 Cl CHF₂ CH₂CF₃ 3-152 Cl CHF₂ CH₂CHF₂ 3-153 Cl CHF₂ CH(Me)-c-Pr 3-154 Cl CHF₂ Pr 3-155 Cl CHF₂ i-Pr 3-156 Cl CHF₂ CH₂CH₂OMe 3-157 Cl CHF₂ CH₂CH₂SMe 3-158 Cl CHF₂ CH₂CN 3-159 Cl CHF₂ CH₂-(tetrahydrofuran-2-yl) 3-160 Cl CHF₂ CH₂C(O)NMe₂ 3-161 Cl CHF₂ Ph 3-162 Cl CHF₂ CH₂-(thien-2-yl) 3-163 Cl CHF₂ Oxetan-3-yl 3-164 Cl CHF₂ c-Bu 3-165 Cl C₂F₅ Me 3-166 Cl C₂F₅ Et 3-167 Cl C₂F₅ c-Pr 3-168 Cl C₂F₅ CH₂-c-Pr 3-169 Cl C₂F₅ CH₂CF₃ 3-170 Cl C₂F₅ CH₂CHF₂ 3-171 Cl Cl Me 3-172 Cl Cl Et 3-173 Cl Cl c-Pr 3-174 Cl Cl CH₂-c-Pr 3-175 Cl Cl CH₂CF₃ 3-176 Cl Cl CH₂CHF₂ 3-177 Cl Br Me 3-178 Cl Br Et 3-179 Cl Br c-Pr 3-180 Cl Br CH₂-c-Pr 3-181 Cl Br CH₂CF₃ 3-182 Cl Br CH₂CHF₂ 3-183 Cl Br CH(Me)-c-Pr 3-184 Cl Br Pr 3-185 Cl Br iPr 3-186 Cl Br CH₂CH₂OMe 3-187 Cl Br CH₂CH₂SMe 3-188 Cl Br CH₂CN 3-189 Cl Br CH₂-(tetrahydrofuran-2-yl) 3-190 Cl Br CH₂C(O)NMe₂ 3-191 Cl Br Ph 3-192 Cl Br CH₂-(thien-2-yl) 3-193 Cl Br Oxetan-3-yl 3-194 Cl Br cBu 3-195 Cl I Me 3-196 Cl I Et 3-197 Cl I c-Pr 3-198 Cl I CH₂-c-Pr 3-199 Cl I CH₂cF₃ 3-200 Cl I CH₂CHF₂ 3-201 Br SO₂Me Me 3-202 Br SO₂Me Et 3-203 Br SO₂Me c-Pr 3-204 Br SO₂Me CH₂-c-Pr 3-205 Br SO₂Me CH₂CF₃ 3-206 Br SO₂Me CH₂CHF₂ 3-207 Br CF₃ Me 3-208 Br CF₃ Et 3-209 Br CF₃ c-Pr 3-210 Br CF₃ CH₂-c-Pr 3-211 Br CF₃ CH₂CF₃ 3-212 Br CF₃ CH₂CHF₂ 3-213 Br CF₃ CH(Me)-c-Pr 3-214 Br CF₃ Pr 3-215 Br CF₃ i-Pr 3-216 Br CF₃ CH₂CH₂OMe 3-217 Br CF₃ CH₂CH₂SMe 3-218 Br CF₃ CH₂CN 3-219 Br CF₃ CH₂-(tetrahydrofuran-2-yl) 3-220 Br CF₃ CH₂C(O)NMe₂ 3-221 Br CF₃ Ph 3-222 Br CF₃ CH₂-(thien-2-yl) 3-223 Br CF₃ Oxetan-3-yl 3-224 Br CF₃ c-Bu 3-225 Br CHF₂ Me 3-226 Br CHF₂ Et 3-227 Br CHF₂ c-Pr 3-228 Br CHF₂ CH₂-c-Pr 3-229 Br CHF₂ CH₂CF₃ 3-230 Br CHF₂ CH₂CHF₂ 3-231 Br C₂F₅ Me 3-232 Br C₂F₅ Et 3-233 Br C₂F₅ c-Pr 3-234 Br C₂F₅ CH₂-c-Pr 3-235 Br C₂F₅ CH₂cF₃ 3-236 Br C₂F₅ CH₂CHF₂ 3-237 I SO₂Me Me 3-238 I SO₂Me Et 3-239 I SO₂Me c-Pr 3-240 I CF₃ Me 3-241 I CF₃ Et 3-242 I CF₃ c-Pr 3-243 I CF₃ CH₂-c-Pr 3-244 I CF₃ CH₂CF₃ 3-245 I CF₃ CH₂CHF₂ 3-246 I CHF₂ Me 3-247 I CHF₂ Et 3-248 I CHF₂ c-Pr 3-249 I CHF₂ CH₂-c-Pr 3-250 I CHF₂ CH₂CF₃ 3-251 I CHF₂ CH₂CHF₂ 3-252 I C₂F₅ Me 3-253 I C₂F₅ Et 3-254 I C₂F₅ c-Pr 3-255 CH₂OMe CF₃ Me 3-256 CH₂OMe CF₃ Et 3-257 CH₂OMe CF₃ c-Pr 3-258 CH₂OMe CF₃ CH₂-c-Pr 3-259 CH₂OMe CF₃ CH₂CF₃ 3-260 CH₂OMe CF₃ CH₂CHF₂ 3-261 CH₂OMe CHF₂ Me 3-262 CH₂OMe CHF₂ Et 3-263 CH₂OMe CHF₂ c-Pr 3-264 CH₂OMe CHF₂ CH₂-c-Pr 3-265 CH₂OMe CHF₂ CH₂CF₃ 3-266 CH₂OMe CHF₂ CH₂CHF₂ 3-267 CH₂OMe CHF₂ c-Pentyl 3-268 CH₂OMe SO₂Me Me 3-269 CH₂OMe SO₂Me Et 3-270 CH₂OMe SO₂Me c-Pr 3-271 Et CF₃ Me 3-272 Et CF₃ Et 3-273 Et CF₃ c-Pr 3-274 Et CF₃ CH₂-c-Pr 3-275 Et CF₃ CH₂CF₃ 3-276 Et CF₃ CH₂CHF₂ 3-277 Et CHF₂ Me 3-278 Et CHF₂ Et 3-279 Et CHF₂ c-Pr 3-280 Et CHF₂ CH₂-c-Pr 3-281 Et CHF₂ CH₂CF₃ 3-282 Et CHF₂ CH₂CHF₂ 3-283 Et C₂F₅ Me 3-284 Et C₂F₅ Et 3-285 Et C₂F₅ c-Pr 3-286 c-Pr CF₃ Me 3-287 c-Pr CF₃ Et 3-288 c-Pr CF₃ c-Pr 3-289 c-Pr CF₃ CH₂-c-Pr 3-290 c-Pr CF₃ CH₂CF₃ 3-291 c-Pr CF₃ CH₂CHF₂ 3-292 c-Pr CF₃ CH(Me)-c-Pr 3-293 c-Pr CF₃ Pr 3-294 c-Pr CF₃ i-Pr 3-295 c-Pr CF₃ CH₂CH₂OMe 3-296 c-Pr CF₃ CH₂CH₂SMe 3-297 c-Pr CF₃ CH₂CN 3-298 c-Pr CF₃ CH₂-(tetrahydrofuran-2-yl) 3-299 c-Pr CF₃ CH₂C(O)NMe₂ 3-300 c-Pr CF₃ Ph 3-301 c-Pr CF₃ CH₂-(thien-2-yl) 3-302 c-Pr CF₃ Oxetan-3-yl 3-303 c-Pr CF₃ c-Bu 3-304 c-Pr CHF₂ Me 3-305 c-Pr CHF₂ Et 3-306 c-Pr CHF₂ c-Pr 3-307 c-Pr CHF₂ CH₂-c-Pr 3-308 c-Pr CHF₂ CH₂cF₃ 3-309 c-Pr CHF₂ CH₂CHF₂ 3-310 c-Pr CHF₂ CH(Me)-c-Pr 3-311 c-Pr CHF₂ Pr 3-312 c-Pr CHF₂ i-Pr 3-313 c-Pr CHF₂ CH₂CH₂OMe 3-314 c-Pr CHF₂ CH₂CH₂SMe 3-315 c-Pr CHF₂ CH₂CN 3-316 c-Pr CHF₂ CH₂-(tetrahydrofuran-2-yl) 3-317 c-Pr CHF₂ CH₂C(O)NMe₂ 3-318 c-Pr CHF₂ Ph 3-319 c-Pr CHF₂ CH₂-(thien-2-yl) 3-320 c-Pr CHF₂ Oxetan-3-yl 3-321 c-Pr CHF₂ c-Bu 3-322 c-Pr C₂F₅ Me 3-323 c-Pr C₂F₅ Et 3-324 c-Pr C₂F₅ c-Pr 3-325 c-Pr C₂F₅ CH₂-c-Pr 3-326 c-Pr C₂F₅ CH₂CF₃ 3-327 c-Pr C₂F₅ CH₂CHF₂ 3-328 c-Pr SO₂Me Me 3-329 c-Pr SO₂Me Et 3-330 c-Pr SO₂Me c-Pr 3-331 CF₃ CF₃ Me 3-332 CF₃ CF₃ Et 3-333 CF₃ CF₃ c-Pr 3-334 CF₃ CF₃ CH₂-c-Pr 3-335 CF₃ CF₃ CH₂CF₃ 3-336 CF₃ CF₃ CH₂CHF₂ 3-337 Cl CF₃ Acetyl 3-338 Cl CF₃ H

TABLE 4 Inventive compounds of the general formula (I) in which Q is Q² and R^(x) is methyl, and the other substituents have the definitions given below.

No. X Y Z 4-1  Me F Me 4-2  Me F Et 4-3  Me F c-Pr 4-4  Me Cl Me 4-5  Me Cl Et 4-6  Me Cl c-Pr 4-7  Me Br Me 4-8  Me Br Et 4-9  Me Br c-Pr 4-10  Me I Me 4-11  Me I Et 4-12  Me I c-Pr 4-13  Me SMe Me 4-14  Me SMe Et 4-15  Me SMe c-Pr 4-16  Me S(O)Me Me 4-17  Me S(O)Me Et 4-18  Me S(O)Me c-Pr 4-19  Me SO₂Me Me 4-20  Me SO₂Me Et 4-21  Me SO₂Me c-Pr 4-22  Me SO₂Me CH₂-c-Pr 4-23  Me SO₂Me CH₂CF₃ 4-24  Me SO₂Me CH₂CHF₂ 4-25  Me CF₃ Me 4-26  Me CF₃ Et 4-27  Me CF₃ c-Pr 4-28  Me CF₃ CH₂-c-Pr 4-29  Me CF₃ CH₂CF₃ 4-30  Me CF₃ CH₂CHF₂ 4-31  Me CHF₂ Me 4-32  Me CHF₂ Et 4-33  Me CHF₂ c-Pr 4-34  Me CHF₂ CH₂-c-Pr 4-35  Me CHF₂ CH₂CF₃ 4-36  Me CHF₂ CH₂CHF₂ 4-37  Me C₂F₅ Me 4-38  Me C₂F₅ Et 4-39  Me C₂F₅ c-Pr 4-40  OMe Cl Me 4-41  OMe Cl Et 4-42  OMe Cl c-Pr 4-43  OMe CF₃ Me 4-44  OMe CF₃ Et 4-45  OMe CF₃ c-Pr 4-46  OMe CF₃ CH₂-c-Pr 4-47  OMe CF₃ CH₂CF₃ 4-48  OMe CF₃ CH₂CHF₂ 4-49  OMe CHF₂ Me 4-50  OMe CHF₂ Et 4-51  OMe CHF₂ c-Pr 4-52  OMe CHF₂ CH₂-c-Pr 4-53  OMe CHF₂ CH₂CF₃ 4-54  OMe CHF₂ CH₂CHF₂ 4-55  SMe SO₂Me Me 4-56  SMe SO₂Me Et 4-57  SMe SO₂Me c-Pr 4-58  SMe CF₃ Me 4-59  SMe CF₃ Et 4-60  SMe CF₃ c-Pr 4-71  SMe CF₃ CH₂-c-Pr 4-72  SMe CF₃ CH₂CF₃ 4-73  SMe CF₃ CH₂CHF₂ 4-74  SMe CHF₂ Me 4-75  SMe CHF₂ Et 4-76  SMe CHF₂ c-Pr 4-77  SMe CHF₂ CH₂-c-Pr 4-78  SMe CHF₂ CH₂CF₃ 4-79  SMe CHF₂ CH₂CHF₂ 4-80  SEt CF₃ Me 4-81  SEt CF₃ Et 4-82  SEt CF₃ c-Pr 4-83  SEt CF₃ CH₂-c-Pr 4-84  SEt CF₃ CH₂CF₃ 4-85  SEt CF₃ CH₂CHF₂ 4-86  SEt CHF₂ Me 4-87  SEt CHF₂ Et 4-88  SEt CHF₂ c-Pr 4-89  SEt CHF₂ CH₂-c-Pr 4-90  SEt CHF₂ CH₂CF₃ 4-91  SEt CHF₂ CH₂CHF₂ 4-92  F CF₃ Me 4-93  F CF₃ Et 4-94  F CF₃ c-Pr 4-95  F CF₃ CH₂-c-Pr 4-96  F CF₃ CH₂CF₃ 4-97  F CF₃ CH₂CHF₂ 4-98  F CHF₂ Me 4-99  F CHF₂ Et 4-100 F CHF₂ c-Pr 4-101 F CHF₂ CH₂-c-Pr 4-102 F CHF₂ CH₂CF₃ 4-103 F CHF₂ CH₂CHF₂ 4-104 Cl SMe Me 4-105 Cl SMe Et 4-106 Cl SMe c-Pr 4-107 Cl S(O)Me Me 4-108 Cl S(O)Me Et 4-109 Cl S(O)Me c-Pr 4-110 Cl SO₂Me Me 4-111 Cl SO₂Me Et 4-112 Cl SO₂Me c-Pr 4-113 Cl SO₂Me CH₂-c-Pr 4-114 Cl SO₂Me CH₂CF₃ 4-115 Cl SO₂Me CH₂CHF₂ 4-116 Cl CF₃ Me 4-117 Cl CF₃ Et 4-118 Cl CF₃ c-Pr 4-119 Cl CF₃ CH₂-c-Pr 4-120 Cl CF₃ CH₂CF₃ 4-121 Cl CF₃ CH₂CHF₂ 4-122 Cl CHF₂ Me 4-123 Cl CHF₂ Et 4-124 Cl CHF₂ c-Pr 4-125 Cl CHF₂ CH₂-c-Pr 4-126 Cl CHF₂ CH₂CF₃ 4-127 Cl CHF₂ CH₂CHF₂ 4-128 Cl C₂F₅ Me 4-129 Cl C₂F₅ Et 4-130 Cl C₂F₅ c-Pr 4-131 Cl C₂F₅ CH₂-c-Pr 4-132 Cl C₂F₅ CH₂CF₃ 4-133 Cl C₂F₅ CH₂CHF₂ 4-134 Cl Cl Me 4-135 Cl Cl Et 4-136 Cl Cl c-Pr 4-137 Cl Cl CH₂-c-Pr 4-138 Cl Cl CH₂CF₃ 4-139 Cl Cl CH₂CHF₂ 4-140 Cl Br Me 4-141 Cl Br Et 4-142 Cl Br c-Pr 4-143 Cl Br CH₂-c-Pr 4-144 Cl Br CH₂CF₃ 4-145 Cl Br CH₂CHF₂ 4-146 Cl I Me 4-147 Cl I Et 4-148 Cl I c-Pr 4-149 Cl I CH₂-c-Pr 4-150 Cl I CH₂CF₃ 4-151 Cl I CH₂CHF₂ 4-152 Br SO₂Me Me 4-153 Br SO₂Me Et 4-154 Br SO₂Me c-Pr 4-155 Br SO₂Me CH₂-c-Pr 4-156 Br SO₂Me CH₂CF₃ 4-157 Br SO₂Me CH₂CHF₂ 4-158 Br CF₃ Me 4-159 Br CF₃ Et 4-160 Br CF₃ c-Pr 4-161 Br CF₃ CH₂-c-Pr 4-162 Br CF₃ CH₂CF₃ 4-163 Br CF₃ CH₂CHF₂ 4-164 Br CHF₂ Me 4-165 Br CHF₂ Et 4-166 Br CHF₂ c-Pr 4-167 Br CHF₂ CH₂-c-Pr 4-168 Br CHF₂ CH₂CF₃ 4-169 Br CHF₂ CH₂CHF₂ 4-170 Br C₂F₅ Me 4-171 Br C₂F₅ Et 4-172 Br C₂F₅ c-Pr 4-173 Br C₂F₅ CH₂-c-Pr 4-174 Br C₂F₅ CH₂CF₃ 4-175 Br C₂F₅ CH₂CHF₂ 4-176 I SO₂Me Me 4-177 I SO₂Me Et 4-178 I SO₂Me c-Pr 4-179 I CF₃ Me 4-180 I CF₃ Et 4-181 I CF₃ c-Pr 4-182 I CF₃ CH₂-c-Pr 4-183 I CF₃ CH₂CF₃ 4-184 I CF₃ CH₂CHF₂ 4-185 I CHF₂ Me 4-186 I CHF₂ Et 4-187 I CHF₂ c-Pr 4-188 I CHF₂ CH₂-c-Pr 4-189 I CHF₂ CH₂CF₃ 4-190 I CHF₂ CH₂CHF₂ 4-191 I C₂F₅ Me 4-192 I C₂F₅ Et 4-193 I C₂F₅ c-Pr 4-194 CH₂OMe CF₃ Me 4-195 CH₂OMe CF₃ Et 4-196 CH₂OMe CF₃ c-Pr 4-197 CH₂OMe CF₃ CH₂-c-Pr 4-198 CH₂OMe CF₃ CH₂CF₃ 4-199 CH₂OMe CF₃ CH₂CHF₂ 4-200 CH₂OMe CHF₂ Me 4-201 CH₂OMe CHF₂ Et 4-202 CH₂OMe CHF₂ c-Pr 4-203 CH₂OMe CHF₂ CH₂-c-Pr 4-204 CH₂OMe CHF₂ CH₂CF₃ 4-205 CH₂OMe CHF₂ CH₂CHF₂ 4-206 CH₂OMe CHF₂ c-Pentyl 4-207 CH₂OMe SO₂Me Me 4-208 CH₂OMe SO₂Me Et 4-209 CH₂OMe SO₂Me c-Pr 4-210 Et CF₃ Me 4-211 Et CF₃ Et 4-212 Et CF₃ c-Pr 4-213 Et CF₃ CH₂-c-Pr 4-214 Et CF₃ CH₂CF₃ 4-215 Et CF₃ CH₂CHF₂ 4-216 Et CHF₂ Me 4-217 Et CHF₂ Et 4-218 Et CHF₂ c-Pr 4-219 Et CHF₂ CH₂-c-Pr 4-220 Et CHF₂ CH₂CF₃ 4-221 Et CHF₂ CH₂CHF₂ 4-222 Et C₂F₅ Me 4-223 Et C₂F₅ Et 4-224 Et C₂F₅ c-Pr 4-225 c-Pr CF₃ Me 4-226 c-Pr CF₃ Et 4-227 c-Pr CF₃ c-Pr 4-228 c-Pr CF₃ CH₂-c-Pr 4-229 c-Pr CF₃ CH₂CF₃ 4-230 c-Pr CF₃ CH₂CHF₂ 4-231 c-Pr CHF₂ Me 4-232 c-Pr CHF₂ Et 4-233 c-Pr CHF₂ c-Pr 4-234 c-Pr CHF₂ CH₂-c-Pr 4-235 c-Pr CHF₂ CH₂CF₃ 4-236 c-Pr CHF₂ CH₂CHF₂ 4-237 c-Pr C₂F₅ Me 4-238 c-Pr C₂F₅ Et 4-239 c-Pr C₂F₅ c-Pr 4-240 c-Pr C₂F₅ CH₂-c-Pr 4-241 c-Pr C₂F₅ CH₂CF₃ 4-242 c-Pr C₂F₅ CH₂CHF₂ 4-243 c-Pr SO₂Me Me 4-244 c-Pr SO₂Me Et 4-245 c-Pr SO₂Me c-Pr 4-246 CF₃ CF₃ Me 4-247 CF₃ CF₃ Et 4-248 CF₃ CF₃ c-Pr 4-249 CF₃ CF₃ CH₂-c-Pr 4-250 CF₃ CF₃ CH₂CF₃ 4-251 CF₃ CF₃ CH₂CHF₂ 4-252 Cl CF₃ H

TABLE 5 Inventive compounds of the general formula (I) in which Q is Q⁴ and R^(z) is hydrogen, and the other substituents have the definitions given below.

No. X Y Z 5-1  Me F Me 5-2  Me F Et 5-3  Me F c-Pr 5-4  Me Cl Me 5-5  Me Cl Et 5-6  Me Cl c-Pr 5-7  Me Br Me 5-8  Me Br Et 5-9  Me Br c-Pr 5-10  Me I Me 5-11  Me I Et 5-12  Me I c-Pr 5-13  Me SMe Me 5-14  Me SMe Et 5-15  Me SMe c-Pr 5-16  Me S(O)Me Me 5-17  Me S(O)Me Et 5-18  Me S(O)Me c-Pr 5-19  Me SO₂Me Me 5-20  Me SO₂Me Et 5-21  Me SO₂Me c-Pr 5-22  Me SO₂Me CH₂-c-Pr 5-23  Me SO₂Me CH₂CF₃ 5-24  Me SO₂Me CH₂CHF₂ 5-25  Me CF₃ Me 5-26  Me CF₃ Et 5-27  Me CF₃ c-Pr 5-28  Me CF₃ CH₂-c-Pr 5-29  Me CF₃ CH₂CF₃ 5-30  Me CF₃ CH₂CHF₂ 5-31  Me CHF₂ Me 5-32  Me CHF₂ Et 5-33  Me CHF₂ c-Pr 5-34  Me CHF₂ CH₂-c-Pr 5-35  Me CHF₂ CH₂CF₃ 5-36  Me CHF₂ CH₂CHF₂ 5-37  Me C₂F₅ Me 5-38  Me C₂F₅ Et 5-39  Me C₂F₅ c-Pr 5-40  OMe Cl Me 5-41  OMe Cl Et 5-42  OMe Cl c-Pr 5-43  OMe CF₃ Me 5-44  OMe CF₃ Et 5-45  OMe CF₃ c-Pr 5-46  OMe CF₃ CH₂-c-Pr 5-47  OMe CF₃ CH₂CF₃ 5-48  OMe CF₃ CH₂CHF₂ 5-49  OMe CHF₂ Me 5-50  OMe CHF₂ Et 5-51  OMe CHF₂ c-Pr 5-52  OMe CHF₂ CH₂-c-Pr 5-53  OMe CHF₂ CH₂CF₃ 5-54  OMe CHF₂ CH₂CHF₂ 5-55  SMe SO₂Me Me 5-56  SMe SO₂Me Et 5-57  SMe SO₂Me c-Pr 5-58  SMe CF₃ Me 5-59  SMe CF₃ Et 5-60  SMe CF₃ c-Pr 5-71  SMe CF₃ CH₂-c-Pr 5-72  SMe CF₃ CH₂CF₃ 5-73  SMe CF₃ CH₂CHF₂ 5-74  SMe CHF₂ Me 5-75  SMe CHF₂ Et 5-76  SMe CHF₂ c-Pr 5-77  SMe CHF₂ CH₂-c-Pr 5-78  SMe CHF₂ CH₂CF₃ 5-79  SMe CHF₂ CH₂CHF₂ 5-80  SEt CF₃ Me 5-81  SEt CF₃ Et 5-82  SEt CF₃ c-Pr 5-83  SEt CF₃ CH₂-c-Pr 5-84  SEt CF₃ CH₂CF₃ 5-85  SEt CF₃ CH₂CHF₂ 5-86  SEt CHF₂ Me 5-87  SEt CHF₂ Et 5-88  SEt CHF₂ c-Pr 5-89  SEt CHF₂ CH₂-c-Pr 5-90  SEt CHF₂ CH₂CF₃ 5-91  SEt CHF₂ CH₂CHF₂ 5-92  F CF₃ Me 5-93  F CF₃ Et 5-94  F CF₃ c-Pr 5-95  F CF₃ CH₂-c-Pr 5-96  F CF₃ CH₂CF₃ 5-97  F CF₃ CH₂CHF₂ 5-98  F CHF₂ Me 5-99  F CHF₂ Et 5-100 F CHF₂ c-Pr 5-101 F CHF₂ CH₂-c-Pr 5-102 F CHF₂ CH₂CF₃ 5-103 F CHF₂ CH₂CHF₂ 5-104 Cl SMe Me 5-105 Cl SMe Et 5-106 Cl SMe c-Pr 5-107 Cl S(O)Me Me 5-108 Cl S(O)Me Et 5-109 Cl S(O)Me c-Pr 5-110 Cl SO₂Me Me 5-111 Cl SO₂Me Et 5-112 Cl SO₂Me c-Pr 5-113 Cl SO₂Me CH₂-c-Pr 5-114 Cl SO₂Me CH₂CF₃ 5-115 Cl SO₂Me CH₂CHF₂ 5-116 Cl CF₃ Me 5-117 Cl CF₃ Et 5-118 Cl CF₃ c-Pr 5-119 Cl CF₃ CH₂-c-Pr 5-120 Cl CF₃ CH₂CF₃ 5-121 Cl CF₃ CH₂CHF₂ 5-122 Cl CHF₂ Me 5-123 Cl CHF₂ Et 5-124 Cl CHF₂ c-Pr 5-125 Cl CHF₂ CH₂-c-Pr 5-126 Cl CHF₂ CH₂CF₃ 5-127 Cl CHF₂ CH₂CHF₂ 5-128 Cl C₂F₅ Me 5-129 Cl C₂F₅ Et 5-130 Cl C₂F₅ c-Pr 5-131 Cl C₂F₅ CH₂-c-Pr 5-132 Cl C₂F₅ CH₂CF₃ 5-133 Cl C₂F₅ CH₂CHF₂ 5-134 Cl Cl Me 5-135 Cl Cl Et 5-136 Cl Cl c-Pr 5-137 Cl Cl CH₂-c-Pr 5-138 Cl Cl CH₂CF₃ 5-139 Cl Cl CH₂CHF₂ 5-140 Cl Br Me 5-141 Cl Br Et 5-142 Cl Br c-Pr 5-143 Cl Br CH₂-c-Pr 5-144 Cl Br CH₂CF₃ 5-145 Cl Br CH₂CHF₂ 5-146 Cl I Me 5-147 Cl I Et 5-148 Cl I c-Pr 5-149 Cl I CH₂-c-Pr 5-150 Cl I CH₂CF₃ 5-151 Cl I CH₂CHF₂ 5-152 Br SO₂Me Me 5-153 Br SO₂Me Et 5-154 Br SO₂Me c-Pr 5-155 Br SO₂Me CH₂-c-Pr 5-156 Br SO₂Me CH₂CF₃ 5-157 Br SO₂Me CH₂CHF₂ 5-158 Br CF₃ Me 5-159 Br CF₃ Et 5-160 Br CF₃ c-Pr 5-161 Br CF₃ CH₂-c-Pr 5-162 Br CF₃ CH₂CF₃ 5-163 Br CF₃ CH₂CHF₂ 5-164 Br CHF₂ Me 5-165 Br CHF₂ Et 5-166 Br CHF₂ c-Pr 5-167 Br CHF₂ CH₂-c-Pr 5-168 Br CHF₂ CH₂CF₃ 5-169 Br CHF₂ CH₂CHF₂ 5-170 Br C₂F₅ Me 5-171 Br C₂F₅ Et 5-172 Br C₂F₅ c-Pr 5-173 Br C₂F₅ CH₂-c-Pr 5-174 Br C₂F₅ CH₂CF₃ 5-175 Br C₂F₅ CH₂CHF₂ 5-176 I SO₂Me Me 5-177 I SO₂Me Et 5-178 I SO₂Me c-Pr 5-179 I CF₃ Me 5-180 I CF₃ Et 5-181 I CF₃ c-Pr 5-182 I CF₃ CH₂-c-Pr 5-183 I CF₃ CH₂CF₃ 5-184 I CF₃ CH₂CHF₂ 5-185 I CHF₂ Me 5-186 I CHF₂ Et 5-187 I CHF₂ c-Pr 5-188 I CHF₂ CH₂-c-Pr 5-189 I CHF₂ CH₂CF₃ 5-190 I CHF₂ CH₂CHF₂ 5-191 I C₂F₅ Me 5-192 I C₂F₅ Et 5-193 I C₂F₅ c-Pr 5-194 CH₂OMe CF₃ Me 5-195 CH₂OMe CF₃ Et 5-196 CH₂OMe CF₃ c-Pr 5-197 CH₂OMe CF₃ CH₂-c-Pr 5-198 CH₂OMe CF₃ CH₂CF₃ 5-199 CH₂OMe CF₃ CH₂CHF₂ 5-200 CH₂OMe CHF₂ Me 5-201 CH₂OMe CHF₂ Et 5-202 CH₂OMe CHF₂ c-Pr 5-203 CH₂OMe CHF₂ CH₂-c-Pr 5-204 CH₂OMe CHF₂ CH₂CF₃ 5-205 CH₂OMe CHF₂ CH₂CHF₂ 5-206 CH₂OMe CHF₂ c-Pentyl 5-207 CH₂OMe SO₂Me Me 5-208 CH₂OMe SO₂Me Et 5-209 CH₂OMe SO₂Me c-Pr 5-210 Et CF₃ Me 5-211 Et CF₃ Et 5-212 Et CF₃ c-Pr 5-213 Et CF₃ CH₂-c-Pr 5-214 Et CF₃ CH₂CF₃ 5-215 Et CF₃ CH₂CHF₂ 5-216 Et CHF₂ Me 5-217 Et CHF₂ Et 5-218 Et CHF₂ c-Pr 5-219 Et CHF₂ CH₂-c-Pr 5-220 Et CHF₂ CH₂CF₃ 5-221 Et CHF₂ CH₂CHF₂ 5-222 Et C₂F₅ Me 5-223 Et C₂F₅ Et 5-224 Et C₂F₅ c-Pr 5-225 c-Pr CF₃ Me 5-226 c-Pr CF₃ Et 5-227 c-Pr CF₃ c-Pr 5-228 c-Pr CF₃ CH₂-c-Pr 5-229 c-Pr CF₃ CH₂CF₃ 5-230 c-Pr CF₃ CH₂CHF₂ 5-231 c-Pr CHF₂ Me 5-232 c-Pr CHF₂ Et 5-233 c-Pr CHF₂ c-Pr 5-234 c-Pr CHF₂ CH₂-c-Pr 5-235 c-Pr CHF₂ CH₂CF₃ 5-236 c-Pr CHF₂ CH₂CHF₂ 5-237 c-Pr C₂F₅ Me 5-238 c-Pr C₂F₅ Et 5-239 c-Pr C₂F₅ c-Pr 5-240 c-Pr C₂F₅ CH₂-c-Pr 5-241 c-Pr C₂F₅ CH₂CF₃ 5-242 c-Pr C₂F₅ CH₂CHF₂ 5-243 c-Pr SO₂Me Me 5-244 c-Pr SO₂Me Et 5-245 c-Pr SO₂Me c-Pr 5-246 CF₃ CF₃ Me 5-247 CF₃ CF₃ Et 5-248 CF₃ CF₃ c-Pr 5-249 CF₃ CF₃ CH₂-c-Pr 5-250 CF₃ CF₃ CH₂CF₃ 5-251 CF₃ CF₃ CH₂CHF₂ 5-252 Cl CF₃ Acetyl 5-253 Cl CF₃ H 5-254 Cl CF₃ CH₂CN 5-255 Cl CF Ph

TABLE 6 Inventive compounds of the general formula (I) in which Q is Q⁴ and R^(z) is methyl, and other substituents have the definitions given below.

No. X Y Z 6-1  Me F Me 6-2  Me F Et 6-3  Me F c-Pr 6-4  Me Cl Me 6-5  Me Cl Et 6-6  Me Cl c-Pr 6-7  Me Br Me 6-8  Me Br Et 6-9  Me Br c-Pr 6-10  Me I Me 6-11  Me I Et 6-12  Me I c-Pr 6-13  Me SMe Me 6-14  Me SMe Et 6-15  Me SMe c-Pr 6-16  Me S(O)Me Me 6-17  Me S(O)Me Et 6-18  Me S(O)Me c-Pr 6-19  Me SO₂Me Me 6-20  Me SO₂Me Et 6-21  Me SO₂Me c-Pr 6-22  Me SO₂Me CH₂-c-Pr 6-23  Me SO₂Me CH₂CF₃ 6-24  Me SO₂Me CH₂CHF₂ 6-25  Me CF₃ Me 6-26  Me CF₃ Et 6-27  Me CF₃ c-Pr 6-28  Me CF₃ CH₂-c-Pr 6-29  Me CF₃ CH₂CF₃ 6-30  Me CF₃ CH₂CHF₂ 6-31  Me CHF₂ Me 6-32  Me CHF₂ Et 6-33  Me CHF₂ c-Pr 6-34  Me CHF₂ CH₂-c-Pr 6-35  Me CHF₂ CH₂CF₃ 6-36  Me CHF₂ CH₂CHF₂ 6-37  Me C₂F₅ Me 6-38  Me C₂F₅ Et 6-39  Me C₂F₅ c-Pr 6-40  OMe Cl Me 6-41  OMe Cl Et 6-42  OMe Cl c-Pr 6-43  OMe CF₃ Me 6-44  OMe CF₃ Et 6-45  OMe CF₃ c-Pr 6-46  OMe CF₃ CH₂-c-Pr 6-47  OMe CF₃ CH₂CF₃ 6-48  OMe CF₃ CH₂CHF₂ 6-49  OMe CHF₂ Me 6-50  OMe CHF₂ Et 6-51  OMe CHF₂ c-Pr 6-52  OMe CHF₂ CH₂-c-Pr 6-53  OMe CHF₂ CH₂CF₃ 6-54  OMe CHF₂ CH₂CHF₂ 6-55  SMe SO₂Me Me 6-56  SMe SO₂Me Et 6-57  SMe SO₂Me c-Pr 6-58  SMe CF₃ Me 6-59  SMe CF₃ Et 6-60  SMe CF₃ c-Pr 6-71  SMe CF₃ CH₂-c-Pr 6-72  SMe CF₃ CH₂CF₃ 6-73  SMe CF₃ CH₂CHF₂ 6-74  SMe CHF₂ Me 6-75  SMe CHF₂ Et 6-76  SMe CHF₂ c-Pr 6-77  SMe CHF₂ CH₂-c-Pr 6-78  SMe CHF₂ CH₂CF₃ 6-79  SMe CHF₂ CH₂CHF₂ 6-80  SEt CF₃ Me 6-81  SEt CF₃ Et 6-82  SEt CF₃ c-Pr 6-83  SEt CF₃ CH₂-c-Pr 6-84  SEt CF₃ CH₂CF₃ 6-85  SEt CF₃ CH₂CHF₂ 6-86  SEt CHF₂ Me 6-87  SEt CHF₂ Et 6-88  SEt CHF₂ c-Pr 6-89  SEt CHF₂ CH₂-c-Pr 6-90  SEt CHF₂ CH₂CF₃ 6-91  SEt CHF₂ CH₂CHF₂ 6-92  F CF₃ Me 6-93  F CF₃ Et 6-94  F CF₃ c-Pr 6-95  F CF₃ CH₂-c-Pr 6-96  F CF₃ CH₂CF₃ 6-97  F CF₃ CH₂CHF₂ 6-98  F CHF₂ Me 6-99  F CHF₂ Et 6-100 F CHF₂ c-Pr 6-101 F CHF₂ CH₂-c-Pr 6-102 F CHF₂ CH₂CF₃ 6-103 F CHF₂ CH₂CHF₂ 6-104 Cl SMe Me 6-105 Cl SMe Et 6-106 Cl SMe c-Pr 6-107 Cl S(O)Me Me 6-108 Cl S(O)Me Et 6-109 Cl S(O)Me c-Pr 6-110 Cl SO₂Me Me 6-111 Cl SO₂Me Et 6-112 Cl SO₂Me c-Pr 6-113 Cl SO₂Me CH₂-c-Pr 6-114 Cl SO₂Me CH₂CF₃ 6-115 Cl SO₂Me CH₂CHF₂ 6-116 Cl CF₃ Me 6-117 Cl CF₃ Et 6-118 Cl CF₃ c-Pr 6-119 Cl CF₃ CH₂-c-Pr 6-120 Cl CF₃ CH₂CF₃ 6-121 Cl CF₃ CH₂CHF₂ 6-122 Cl CHF₂ Me 6-123 Cl CHF₂ Et 6-124 Cl CHF₂ c-Pr 6-125 Cl CHF₂ CH₂-c-Pr 6-126 Cl CHF₂ CH₂CF₃ 6-127 Cl CHF₂ CH₂CHF₂ 6-128 Cl C₂F₅ Me 6-129 Cl C₂F₅ Et 6-130 Cl C₂F₅ c-Pr 6-131 Cl C₂F₅ CH₂-c-Pr 6-132 Cl C₂F₅ CH₂CF₃ 6-133 Cl C₂F₅ CH₂CHF₂ 6-134 Cl Cl Me 6-135 Cl Cl Et 6-136 Cl Cl c-Pr 6-137 Cl Cl CH₂-c-Pr 6-138 Cl Cl CH₂CF₃ 6-139 Cl Cl CH₂CHF₂ 6-140 Cl Br Me 6-141 Cl Br Et 6-142 Cl Br c-Pr 6-143 Cl Br CH₂-c-Pr 6-144 Cl Br CH₂CF₃ 6-145 Cl Br CH₂CHF₂ 6-146 Cl I Me 6-147 Cl I Et 6-148 Cl I c-Pr 6-149 Cl I CH₂-c-Pr 6-150 Cl I CH₂CF₃ 6-151 Cl I CH₂CHF₂ 6-152 Br SO₂Me Me 6-153 Br SO₂Me Et 6-154 Br SO₂Me c-Pr 6-155 Br SO₂Me CH₂-c-Pr 6-156 Br SO₂Me CH₂CF₃ 6-157 Br SO₂Me CH₂CHF₂ 6-158 Br CF₃ Me 6-159 Br CF₃ Et 6-160 Br CF₃ c-Pr 6-161 Br CF₃ CH₂-c-Pr 6-162 Br CF₃ CH₂CF₃ 6-163 Br CF₃ CH₂CHF₂ 6-164 Br CHF₂ Me 6-165 Br CHF₂ Et 6-166 Br CHF₂ c-Pr 6-167 Br CHF₂ CH₂-c-Pr 6-168 Br CHF₂ CH₂CF₃ 6-169 Br CHF₂ CH₂CHF₂ 6-170 Br C₂F₅ Me 6-171 Br C₂F₅ Et 6-172 Br C₂F₅ c-Pr 6-173 Br C₂F₅ CH₂-c-Pr 6-174 Br C₂F₅ CH₂CF₃ 6-175 Br C₂F₅ CH₂CHF₂ 6-176 I SO₂Me Me 6-177 I SO₂Me Et 6-178 I SO₂Me c-Pr 6-179 I CF₃ Me 6-180 I CF₃ Et 6-181 I CF₃ c-Pr 6-182 I CF₃ CH₂-c-Pr 6-183 I CF₃ CH₂CF₃ 6-184 I CF₃ CH₂CHF₂ 6-185 I CHF₂ Me 6-186 I CHF₂ Et 6-187 I CHF₂ c-Pr 6-188 I CHF₂ CH₂-c-Pr 6-189 I CHF₂ CH₂CF₃ 6-190 I CHF₂ CH₂CHF₂ 6-191 I C₂F₅ Me 6-192 I C₂F₅ Et 6-193 I C₂F₅ c-Pr 6-194 CH₂OMe CF₃ Me 6-195 CH₂OMe CF₃ Et 6-196 CH₂OMe CF₃ c-Pr 6-197 CH₂OMe CF₃ CH₂-c-Pr 6-198 CH₂OMe CF₃ CH₂CF₃ 6-199 CH₂OMe CF₃ CH₂CHF₂ 6-200 CH₂OMe CHF₂ Me 6-201 CH₂OMe CHF₂ Et 6-202 CH₂OMe CHF₂ c-Pr 6-203 CH₂OMe CHF₂ CH₂-c-Pr 6-204 CH₂OMe CHF₂ CH₂CF₃ 6-205 CH₂OMe CHF₂ CH₂CHF₂ 6-206 CH₂OMe CHF₂ c-Pentyl 6-207 CH₂OMe SO₂Me Me 6-208 CH₂OMe SO₂Me Et 6-209 CH₂OMe SO₂Me c-Pr 6-210 Et CF₃ Me 6-211 Et CF₃ Et 6-212 Et CF₃ c-Pr 6-213 Et CF₃ CH₂-c-Pr 6-214 Et CF₃ CH₂CF₃ 6-215 Et CF₃ CH₂CHF₂ 6-216 Et CHF₂ Me 6-217 Et CHF₂ Et 6-218 Et CHF₂ c-Pr 6-219 Et CHF₂ CH₂-c-Pr 6-220 Et CHF₂ CH₂CF₃ 6-221 Et CHF₂ CH₂CHF₂ 6-222 Et C₂F₅ Me 6-223 Et C₂F₅ Et 6-224 Et C₂F₅ c-Pr 6-225 c-Pr CF₃ Me 6-226 c-Pr CF₃ Et 6-227 c-Pr CF₃ c-Pr 6-228 c-Pr CF₃ CH₂-c-Pr 6-229 c-Pr CF₃ CH₂CF₃ 6-230 c-Pr CF₃ CH₂CHF₂ 6-231 c-Pr CHF₂ Me 6-232 c-Pr CHF₂ Et 6-233 c-Pr CHF₂ c-Pr 6-234 c-Pr CHF₂ CH₂-c-Pr 6-235 c-Pr CHF₂ CH₂CF₃ 6-236 c-Pr CHF₂ CH₂CHF₂ 6-237 c-Pr C₂F₅ Me 6-238 c-Pr C₂F₅ Et 6-239 c-Pr C₂F₅ c-Pr 6-240 c-Pr C₂F₅ CH₂-c-Pr 6-241 c-Pr C₂F₅ CH₂CF₃ 6-242 c-Pr C₂F₅ CH₂CHF₂ 6-243 c-Pr SO₂Me Me 6-244 c-Pr SO₂Me Et 6-245 c-Pr SO₂Me c-Pr 6-246 CF₃ CF₃ Me 6-247 CF₃ CF₃ Et 6-248 CF₃ CF₃ c-Pr 6-249 CF₃ CF₃ CH₂-c-Pr 6-250 CF₃ CF₃ CH₂CF₃ 6-251 CF₃ CF₃ CH₂CHF₂ 6-252 Cl CF₃ Acetyl 6-253 Cl CF₃ H 6-254 Cl CF₃ CH(Me)-c-Pr 6-255 Me CF₃ iPr 6-256 Me CF₃ cBu 6-257 Cl Br CH(Me)-c-Pr 6-258 Me CHF₂ CH(Me)-c-Pr 6-259 Cl CHF₂ Pr 6-260 Cl CHF₂ i-Pr 6-261 Cl CHF₂ c-Bu 6-262 Cl CHF₂ CH₂CH₂OMe 6-263 Cl CHF₂ CH₂-(tetrahydrofuran-₂-yl) 6-264 Cl CHF₂ CH₂-(thien-₂-yl) 6-265 Cl CHF₂ CH₂C(O)NMe₂ 6-266 Cl CHF₂ Ph 6-267 Br CHF₂ CH(Me)-c-Pr 6-268 c-Pr CF CH(Me)-c-Pr

NMR data for numerous inventive compounds of the formula (I) mentioned in tables above are disclosed below for further characterization:

Ex. no. 1-4: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.63 (br s, 1H); 8.50 (q, 1H); 7.67 (d, 1H); 7.50 (d, 1H); 3.98 (s, 3H); 2.80 (d, 3H); 2.33 (s, 3H);

Ex. no. 1-19: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.57 (q, 1H); 7.94 (d, 1H); 7.89 (d, 1H); 4.01 (s, 3H); 3.27 (s, 3H); 2.78 (d, 3H); 2.35 (s, 3H);

Ex. no. 1-20: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.63 (t, 1H); 7.94 (d, 1H); 7.88 (d, 1H); 4.01 (s, 3H); 3.27 (m, 2H); 3.27 (s, 3H); 2.38 (s, 3H); 1.13 (t, 3H);

Ex. no. 1-21: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.81 (br s, 1H); 8.70 (d, 1H); 7.93 (d, 1H); 7.88 (d, 1H); 4.00 (s, 3H); 3.27 (s, 3H); 2.78 (m, 1H); 2.35 (s, 3H); 0.69 (m, 2H); 0.62 (m, 1H); 0.51 (m, 1H);

Ex. no. 1-25: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.51 (q, 1H); 7.83 (d, 1H); 7.76 (d, 1H); 4.00 (s, 3H); 2.79 (d, 3H); 2.34 (s, 3H);

Ex. no. 1-26: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.49 (t, 1H); 7.83 (d, 1H); 7.75 (d, 1H); 4.00 (s, 3H); 3.28 (m, 2H); 2.36 (s, 3H); 1.11 (t, 3H);

Ex. no. 1-27: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.75 (br s, 1H); 8.66 (d, 1H); 7.83 (d, 1H); 7.75 (d, 1H); 4.00 (s, 3H); 2.81 (m, 1H); 2.34 (s, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 1-28: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.72 (t, 1H); 7.83 (d, 1H); 7.76 (d, 1H); 4.01 (s, 3H); 3.13 (m, 2H); 2.38 (s, 3H); 1.01 (m, 1H); 0.45 (m, 2H); 0.23 (m, 2H);

Ex. no. 1-29: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.80 (br s, 1H); 9.38 (t, 1H); 7.88 (d, 1H); 7.80 (d, 1H); 4.13 (m, 2H); 4.01 (s, 3H); 2.35 (s, 3H);

Ex. no. 1-30: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 9.09 (t, 1H); 7.86 (d, 1H); 7.78 (d, 1H); 6.13 (tt, 1H); 4.01 (s, 3H); 3.71 (2H); 2.36 (s, 3H);

Ex. no. 1-31: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 8.62 (t, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 4.01 (s, 3H); 3.40 (m, 1H); 2.39 (d, 3H); 1.20 (dd, 3H); 0.91 (m, 1H); 0.44 (m, 2H); 0.29 (m, 2H);

Ex. no. 1-32: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 8.81 (t, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.95 (t, 1H); 4.01 (s, 3H); 3.24 (m, 2H); 1.54 (m, 2H); 0.92 (t, 3H);

Ex. no. 1-33: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.77 (br s, 1H); 8.51 (d, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 4.08 (m, 1H); 4.00 (s, 3H); 2.37 (s, 3H); 1.16 (d, 3H); 1.12 (d, 3H);

Ex. no. 1-34: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.70 (d, 1H); 7.83 (d, 1H); 7.75 (d, 1H); 4.00 (s, 3H); 3.52-3.31 (m, 4H); 3.27 (s, 3H); 2.36 (s, 3H);

Ex. no. 1-36: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.81 (br s, 1H); 9.42 (t, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 4.49 (m, 2H); 4.01 (s, 3H); 2.35 (s, 3H);

Ex. no. 1-37: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.77 (br s, 1H); 8.72 (br s, 1H); 7.83 (d, 1H); 7.75 (d, 1H); 4.00 (s, 3H); 3.97 (m, 1H); 3.77 (m, 1H); 3.63 (m, 1H); 3.35 (m, 1H); 3.27 (m, 1H); 2.36 (s, 3H); 1.92 (m, 1H); 1.83 (m, 2H); 1.60 (m, 1H);

Ex. no. 1-41: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 9.41 (d, 1H); 7.87 (d, 1H); 7.80 (d, 1H); 4.98 (m, 1H); 4.80 (t, 2H); 4.54 (t, 1H); 4.48 (t, 1H); 4.01 (s, 3H); 2.36 (s, 3H);

Ex. no. 1-44: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.56 (q, 1H); 7.80 (d, 1H); 7.63 (d, 1H); 6.91 (t, 1H); 4.00 (t, 1H); 2.80 (d, 3H); 2.33 (s, 3H);

Ex. no. 1-45: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.65 (t, 1H); 7.79 (d, 1H); 7.63 (d, 1H); 6.91 (t, 1H); 4.00 (s, 3H); 3.30 (m, 2H); 2.35 (s, 3H); 1.13 (t, 3H);

Ex. no. 1-46: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.68 (br s, 1H); 8.71 (d, 1H); 7.79 (d, 1H); 7.62 (d, 1H); 6.90 (t, 1H); 3.99 (s, 3H); 2.85 (m, 1H); 2.33 (s, 3H); 0.71 (m, 1H); 0.54 (m, 2H);

Ex. no. 1-47: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.79 (t, 1H); 7.80 (d, 1H); 7.64 (d, 1H); 6.92 (t, 1H); 4.00 (s, 3H); 3.15 (m, 2H); 2.38 (s, 3H); 1.04 (m, 1H); 0.46 (m, 2H); 0.24 (m, 2H);

Ex. no. 1-49: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 9.12 (t, 1H); 7.82 (d, 1H); 7.66 (d, 1H); 6.93 (t, 1H); 6.19 (tt, 1H); 4.00 (s, 3H); 3.72 (m, 2H); 2.36 (s, 3H);

Ex. no. 1-56: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.66 (br s, 1H); 8.53 (q, 1H); 7.89 (d, 1H); 7.67 (d, 1H); 3.99 (s, 3H); 3.86 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-57: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.60 (t, 1H); 7.88 (d, 1H); 7.67 (d, 1H); 3.99 (s, 3H); 3.87 (s, 3H); 3.29 (m, 2H); 1.11 (t, 3H);

Ex. no. 1-58: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.68 (d, 1H); 7.88 (d, 1H); 7.66 (d, 1H); 3.99 (s, 3H); 3.86 (s, 3H); 2.80 (m, 1H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 1-72: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.53 (br s, 1H); 8.57 (q, 1H); 7.85 (d, 1H); 7.54 (d, 1H); 6.96 (t, 1H); 3.99 (s, 3H); 3.85 (s, 3H); 2.81 (d, 3H);

Ex. no. 1-73: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.52 (br s, 1H); 8.65 (t, 1H); 7.84 (d, 1H); 7.54 (d, 1H); 6.96 (t, 1H); 3.99 (s, 3H); 3.86 (s, 3H); 3.20 (m, 2H); 1.13 (t, 3H);

Ex. no. 1-74: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.51 (br s, 1H); 8.72 (d, 1H); 7.84 (d, 1H); 7.52 (d, 1H); 6.95 (t, 1H); 3.98 (s, 3H); 3.85 (s, 3H); 2.85 (m, 1H); 0.71 (m, 2H); 0.54 (m, 2H);

Ex. no. 1-81: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.48 (q, 1H); 7.95 (d, 1H); 7.88 (d, 1H); 4.05 (s, 3H); 2.80 (d, 3H); 2.43 (s, 3H);

Ex. no. 1-82: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.56 (t, 1H); 7.95 (d, 1H); 7.88 (d, 1H); 4.06 (s, 3H); 3.32 (m, 2H); 2.44 (s, 3H); 1.14 (t, 3H);

Ex. no. 1-83: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.83 (br s, 1H); 8.64 (d, 1H); 7.94 (d, 1H); 7.88 (d, 1H); 4.05 (s, 3H); 2.80 (m, 1H); 2.43 (s, 3H); 0.71 (m, 2H); 0.53 (br s, 2H);

Ex. no. 1-84: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.83 (br s, 1H); 8.68 (t, 1H); 7.95 (d, 1H); 7.87 (d, 1H); 4.05 (s, 3H); 3.16 (m, 2H); 2.45 (s, 3H); 1.02 (m, 1H); 0.45 (m, 2H); 0.24 (m, 2H);

Ex. no. 1-86: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.85 (br s, 1H); 9.10 (t, 1H); 7.98 (d, 1H); 7.92 (d, 1H); 6.11 (tt, 1H); 4.05 (s, 3H); 3.71 (m, 2H); 2.43 (s, 3H);

Ex. no. 1-87: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.54 (q, 1H); 7.81 (s, 2H); 6.90 (t, 1H); 4.04 (s, 3H); 2.82 (d, 3H); 2.42 (s, 3H);

Ex. no. 1-88: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.62 (t, 1H); 7.82 (s, 2H); 6.91 (t, 1H); 4.05 (s, 3H); 3.33 (m, 2H); 2.43 (s, 3H); 1.16 (t, 3H);

Ex. no. 1-89: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.77 (br s, 1H); 8.70 (d, 1H); 7.81 (br s, 2H); 6.90 (t, 1H); 4.05 (s, 3H); 2.85 (m, 1H); 2.41 (s, 3H); 0.71 (m, 2H); 0.58 (m, 2H);

Ex. no. 1-90: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.77 (br s, 1H); 8.76 (t, 1H); 7.82 (br s, 1H); 6.91 (t, 1H); 4.05 (s, 3H); 3.18 (m, 2H); 2.44 (s, 3H); 1.06 (m, 1H); 0.46 (m, 2H); 0.26 (m, 2H);

Ex. no. 1-92: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 9.14 (t, 1H); 7.85 (br s, 2H); 6.92 (t, 1H); 6.18 (tt, 1H); 4.05 (s, 3H); 3.73 (m, 2H); 2.42 (s, 3H);

Ex. no. 1-123: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.03 (br s, 1H); 8.72 (q, 1); 8.07 (d, 1H); 8.02 (d, 1H); 4.01 (s, 3H); 3.31 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-125: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.02 (br s, 1H); 8.85 (d, 1H); 8.06 (d, 1H); 8.02 (d, 1H); 4.01 (s, 3H); 3.31 (s, 3H); 2.78 (m, 1H); 0.70 (m, 2H); 0.60 (m, 1H); 0.56 (m, 1H);

Ex. no. 1-129: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.00 (br s, 1H); 8.69 (q, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-130: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.76 (t, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.01 (s, 3H); 3.29 (m, 2H); 1.11 (t, 3H);

Ex. no. 1-131: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.82 (d, 1H); 7.97 (d, 1H); 7.92 (d, 1H); 4.01 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.50 (br s, 2H);

Ex. no. 1-132: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.02 (br s, 1H); 8.89 (t, 1H); 7.98 (d, 1H); 7.93 (d, 1H); 4.02 (s, 3H); 3.15 (m, 2H); 1.00 (m, 1H); 0.45 (m, 2H); 0.24 (m, 2H)

Ex. no. 1-133: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.06 (br s, 1H); 9.56 (t, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.16 (m, 2H); 4.02 (s, 3H);

Ex. no. 1-134: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.05 (br s, 1H); 9.29 (t, 1H); 8.02 (d, 1H); 7.96 (d, 1H); 6.12 (tt, 1H); 4.02 (s, 3H); 3.72 (m, 2H);

Ex. no. 1-135: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.02 (br s, 1H); 8.77 (d, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.02 (s, 3H); 3.44 (m, 1H); 1.20 (m, 3H); 0.90 (m, 1H); 0.43 (m, 2H); 0.29 (m, 2H);

Ex. no. 1-136: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.78 (t, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.02 (s, 3H); 3.22 (m, 2H); 1.53 (m, 2H); 0.92 (t, 3H);

Ex. no. 1-137: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.66 (d, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.07 (m, 1H); 4.01 (s, 3H); 1.14 (br s, 6H);

Ex. no. 1-138: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.00 (br s, 1H); 8.91 (t, 1H); 7.97 (d, 1H); 7.92 (d, 1); 4.01 (s, 3H); 3.43 (m, 4H); 3.27 (s, 3H);

Ex. no. 1-139: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.02 (br s, 1H); 8.99 (t, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 4.01 (s, 3H); 3.45 (m, 2H); 2.63 (t, 2H); 2.11 (s, 3H);

Ex. no. 1-140: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.05 (br s, 1H); 9.61 (t, 1H); 8.04 (d, 1H); 7.99 (d, 1H); 4.42 (d, 2H); 4.01 (s, 3H);

Ex. no. 1-141: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.00 (br s, 1H); 8.90 (t, 1H); 7.97 (d, 1H); 7.92 (d, 1H); 4.01 (s, 3H); 3.95 (m, 1H); 3.77 (m, 1H); 3.63 (m, 1H); 3.30 (m, 2H); 1.95 (m, 1H); 1.83 (m, 2H); 1.63 (m, 1H);

Ex. no. 1-142: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.90 (t, 1H); 7.96 (d, 1H); 7.91 (d, 1H); 4.18 (br d, 2H); 4.01 (s, 3H); 3.00 (s, 3H); 2.86 (s, 3H);

Ex. no. 1-143: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.08 (br s, 1H); 10.86 (br s, 1H); 8.04 (m, 2H); 7.65 (d, 2H); 7.38 (m, 2H); 7.15 (t, 1H); 4.02 (s, 3H);

Ex. no. 1-144: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 9.36 (t, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 7.45 (m, 1H); 7.07 (m, 1H); 6.98 (m, 1H); 4.66 (br s, 2H); 4.01 (s, 3H);

Ex. no. 1-146: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 9.01 (d, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.35 (m, 1H); 4.01 (s, 3H); 2.25 (m, 2H); 1.98 (m, 2H); 1.70 (m, 2H);

Ex. no. 1-147: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 8.72 (q, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.01 (s, 3H); 2.81 (d, 3H);

Ex. no. 1-148: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 8.78 (t, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.95 (t, 1H); 4.01 (s, 3H); 3.31 (m, 2H); 1.13 (t, 3H);

Ex. no. 1-149: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.92 (br s, 1H); 8.85 (d, 1H); 7.90 (d, 1H); 7.77 (d, 1H); 6.95 (t, 1H); 4.00 (s, 3H); 2.83 (m, 1H); 0.72 (m, 2H); 0.55 (m, 2H);

Ex. no. 1-155: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 8.70 (d, 1H); 7.90 (d, 1H); 7.77 (d, 1H); 6.94 (t, 1H); 4.09 (m, 1H); 4.01 (s, 3H); 1.16 (d, 6H);

Ex. no. 1-156: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 8.92 (t, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.01 (s, 3H); 3.46 (m, 4H); 3.29 (s, 3H);

Ex. no. 1-157: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.95 (br s, 1H); 8.99 (t, 1H); 7.92 (d, 1H); 7.80 (d, 1H); 7.05 (t, 1H); 4.01 (s, 3H); 3.49 (m, 2H); 2.67 (m, 2H); 2.12 (s, 3H);

Ex. no. 1-158: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.98 (br s, 1H); 9.59 (t, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.40 (d, 2H); 4.01 (s, 3H);

Ex. no. 1-159: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 8.94 (t, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.97 (t, 1H); 4.01 (s, 3H); 3.98 (m, 1H); 3.78 (m, 1H); 3.64 (m, 1H); 3.35 (m, 2H); 1.95 (m, 1H); 1.84 (m, 2H); 1.62 (m, 1H);

Ex. no. 1-160: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.95 (br s, 1H); 9.12 (t, 1H); 7.94 (d, 1H); 7.83 (d, 1H); 7.58 (t, 1H); 4.17 (d, 2H); 4.01 (t, 3H); 3.02 (s, 3H); 2.89 (s, 3H);

Ex. no. 1-161: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 10.84 (br s, 1H); 7.99 (d, 1H); 7.85 (d, 1H); 7.69 (m, 2H); 7.38 (m, 2H); 7.15 (m, 1H); 7.12 (t, 1H); 4.02 (s, 3H);

Ex. no. 1-162: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.95 (br s, 1H); 9.45 (t, 1H); 7.93 (d, 1H); 7.79 (d, 1H); 7.45 (m, 1H); 7.08 (m, 1H); 6.99 (m, 1H); 6.92 (t, 1H); 4.68 (d, 2H); 4.00 (s, 3H);

Ex. no. 1-164: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 9.05 (d, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.93 (t, 1H); 4.37 (m, 1H); 4.01 (s, 3H); 2.26 (m, 2H); 2.01 (m, 2H); 1.72 (m, 2H);

Ex. no. 1-165: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.61 (q, 1H); 8.00 (d, 1H); 7.85 (d, 1H); 4.01 (s, 3H); 2.78 (d, 3H);

Ex. no. 1-166: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.67 (t, 1H); 7.99 (d, 1H); 7.85 (d, 1H); 4.01 (s, 3H); 3.29 (m, 1H); 1.11 (t, 3H);

Ex. no. 1-173: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 8.79 (d, 1H); 7.77 (d, 1H); 7.66 (d, 1H); 3.99 (s, 3H); 2.82 (m, 1H); 0.72 (m, 2H); 0.52 (m, 2H);

Ex. no. 1-177: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 8.65 (q, 1H); 7.81 (d, 1H); 7.69 (d, 1H); 3.99 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-178: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 8.71 (t, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.28 (m, 2H); 1.14 (t, 3H);

Ex. no. 1-179: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.77 (d, 1H); 7.80 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 2.81 (m, 1H); 0.72 (m, 2H); 0.54 (d, 2H);

Ex. no. 1-180: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 8.80 (t, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.16 (m, 2H); 1.02 (m, 1H); 0.46 (m, 2H); 0.26 (m, 2H);

Ex. no. 1-181: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 9.49 (t, 1H); 7.85 (d, 1H); 7.74 (d, 1H); 4.14 (m, 2H); 3.99 (s, 3H);

Ex. no. 1-182: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 9.23 (t, 1H); 7.83 (d, 1H); 7.72 (d, 1H); 6.14 (tt, 1H); 3.99 (s, 3H); 3.70 (m, 2H);

Ex. no. 1-183: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.66 (d, 1H); 7.80 (d, 1H); 7.67 (d, 1H); 3.99 (s, 3H); 3.49 (m, 1H); 1.22 (d, 3H); 0.92 (m, 1H); 0.43 (m, 2H); 0.32 (m, 2H);

Ex. no. 1-184: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.72 (t, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.21 (m, 2H); 1.55 (m, 2H); 0.94 (t, 3H);

Ex. no. 1-185: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.61 (d, 1H); 7.80 (d, 1H); 7.67 (d, 1H); 4.05 (m, 1H); 3.99 (s, 3H); 1.17 (d, 6H);

Ex. no. 1-186: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.86 (t, 1H); 7.80 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.47 (m, 2H); 3.41 (m, 2H); 3.28 (s, 3H);

Ex. no. 1-187: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.93 (t, 1H); 7.81 (d, 1H); 7.69 (d, 1H); 3.99 (s, 3H); 3.44 (m, 2H); 2.66 (m, 2H); 2.12 (s, 3H);

Ex. no. 1-195: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.86 (br s, 1H); 8.58 (q, 1H); 7.98 (d, 1H); 7.47 (d, 1H); 3.98 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-196: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.85 (br s, 1H); 8.64 (t, 1H); 7.98 (d, 1H); 7.47 (d, 1H); 3.99 (s, 3H); 3.27 (m, 2H); 1.15 (t, 3H);

Ex. no. 1-197: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.86 (br s, 1H); 8.70 (d, 1H); 7.97 (d, 1H); 7.46 (d, 1H); 3.98 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.57 (br s, 2H);

Ex. no. 1-207: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.67 (q, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.03 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-208: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.72 (t, 1H); 7.91 (d, 1H); 7.96 (d, 1H); 4.03 (s, 3H); 3.29 (m, 2H); 1.12 (t, 3H);

Ex. no. 1-209: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.00 (br s, 1H); 8.81 (d, 1H); 7.96 (d, 1H); 7.91 (d, 1H); 4.03 (s, 3H); 2.79 (m, 1H); 0.72 (m, 2H); 0.57 (m, 1H); 0.48 (m, 1H);

Ex. no. 1-210: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.99 (br s, 1H); 8.84 (t, 1H); 7.96 (d, 1H); 7.91 (d, 1H); 4.03 (s, 3H); 3.14 (m, 2H); 1.01 (m, 1H); 0.45 (m, 2H); 0.24 (m, 2H);

Ex. no. 1-211: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 9.52 (t, 1H); 8.01 (d, 1H); 7.97 (d, 1H); 4.20 (m, 1H); 4.08 (m, 1H); 4.04 (s, 3H);

Ex. no. 1-212: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 9.26 (t, 1H); 7.99 (d, 1H); 7.95 (d, 1H); 6.12 (tt, 1H); 4.03 (s, 3H); 3.70 (m, 2H);

Ex. no. 1-225: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.70 (q, 1H); 7.86 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.03 (s, 3H); 2.81 (d, 3H);

Ex. no. 1-226: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.77 (t, 1H); 7.86 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.03 (s, 3H); 3.29 (m, 2H); 1.14 (t, 3H);

Ex. no. 1-227: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.92 (br s, 1H); 8.83 (d, 1H); 7.85 (d, 1H); 7.80 (d, 1H); 6.93 (t, 1H); 4.02 (s, 3H); 2.83 (m, 1H); 0.71 (m, 2H); 0.57 (m, 2H);

Ex. no. 1-228: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 8.90 (t, 1H); 7.86 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.03 (s, 3H); 3.16 (m, 2H); 1.04 (m, 1H); 0.46 (m, 2H); 0.26 (m, 2H);

Ex. no. 1-229: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.96 (br s, 1H); 9.54 (t, 1H); 7.91 (d, 1H); 7.84 (d, 1H); 6.92 (t, 1H); 4.14 (m, 2H); 4.03 (s, 3H);

Ex. no. 1-230: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.95 (br s, 1H); 9.28 (t, 1H); 7.90 (d, 1H); 7.83 (d, 1H); 6.94 (t, 1H); 6.18 (tt, 1H); 4.03 (s, 3H); 3.72 (m, 2H);

Ex. no. 1-271: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.81 (br s, 1H); 8.52 (q, 1H); 7.85 (d, 1H); 7.78 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H); 2.72 (m, 2H); 1.17 (t, 3H);

Ex. no. 1-272: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.80 (br s, 1H); 8.62 (t, 1H); 7.84 (d, 1H); 7.77 (d, 1H); 4.01 (s, 3H); 3.29 (q, 2H); 2.77 (m, 2H); 1.18 (t, 3H); 1.11 (t, 3H);

Ex. no. 1-273: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.68 (d, 1H); 7.84 (d, 1H); 7.76 (d, 1H); 4.01 (s, 3H); 2.81 (m, 2H) M 2.70 (m, 1H); 1.17 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 1-274: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.80 (br s, 1H); 8.74 (t, 1H); 7.84 (d, 1H); 7.76 (d, 1H); 4.01 (s, 3H); 3.19 (m, 1H); 3.08 (m, 1H); 2.80 (m, 2H); 1.20 (t, 3H); 1.02 (m, 1H); 0.45 (m, 2H); 0.24 (m, 2H);

Ex. no. 1-276: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 9.10 (t, 1H); 7.88 (d, 1H); 7.79 (d, 1H); 6.13 (tt, 1H); 4.01 (s, 3H); 3.77 (m, 1H); 3.63 (m, 1H); 2.77 (m, 2H); 1.17 (t, 3H);

Ex. no. 1-277: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.73 (br s, 1H); 8.57 (q, 3H); 7.80 (d, 1H); 7.64 (d, 1H); 6.89 (t, 1H); 4.00 (s, 3H); 2.81 (d, 3H); 2.74 (q, 2H); 1.15 (t, 3H);

Ex. no. 1-278: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.72 (br s, 1H); 8.67 (t, 1H); 7.80 (d, 1H); 7.64 (d, 1H); 6.90 (t, 1H); 4.00 (s, 3H); 3.21 (m, 2H); 2.76 (q, 2H); 1.15 (2x t, 6H)

Ex. no. 1-279: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.72 (br s, 1H); 8.75 (d, 1H); 7.80 (d, 1H); 7.63 (d, 1H); 6.89 (t, 1H); 4.00 (s, 3H); 2.86 (m, 1H); 2.75 (m, 2H); 1.15 (t, 3H); 0.71 (m, 2H); 0.53 (m, 2H);

Ex. no. 1-286: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.44 (q, 1H); 7.77 (br s, 2H); 4.03 (s, 3H); 2.79 (d, 3H); 2.11 (m, 1H); 0.84 (m, 2H); 0.64 (m, 2H);

Ex. no. 1-287: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.51 (t, 1H); 7.77 (br s, 2H); 4.03 (s, 3H); 3.29 (m, 2H); 2.14 (m, 1H); 1.13 (t, 3H); 0.84 (m, 2H); 0.66 (m, 2H);

Ex. no. 1-288: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.59 (d, 1H); 7.77 (br s, 2H); 4.03 (s, 3H); 2.79 (m, 1H); 2.11 (m, 1H); 0.85 (m, 2H); 0.70 (m, 2H); 0.66 (m, 2H); 0.51 (m, 2H);

Ex. no. 1-289: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.63 (t, 1H); 7.77 (br s, 2H); 4.03 (s, 3H); 3.13 (m, 2H); 2.15 (m, 1H); 1.03 (m, 1H); 0.85 (m, 2H); 0.68 (m, 2H); 0.45 (m, 2H); 0.23 (m, 2H);

Ex. no. 1-291: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.72 (br s, 1H); 9.03 (t, 1H); 7.80 (br s, 2H); 6.13 (tt, 1H); 4.04 (s, 3H); 3.69 (m, 2H); 2.13 (m, 1H); 0.87 (m, 2H); 0.64 (m, 2H);

Ex. no. 1-292: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.55 (d, 1H); 7.76 (br s, 2H); 4.03 (s, 3H); 3.38 (m, 1H); 2.18 (m, 1H); 1.21 (d, 3H); 0.89 (m, 3H); 0.69 (m, 2H); 0.44 (m, 2H); 0.34 (m, 1H); 0.24 (m, 1H);

Ex. no. 1-304: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.64 (br s, 1H); 8.52 (q, 1H); 7.73 (d, 1H); 7.66 (d, 1H); 6.94 (t, 1H); 4.03 (s, 3H); 2.81 (d, 3H); 2.17 (m, 1H); 0.83 (m, 2H); 0.58 (m, 2H);

Ex. no. 1-305: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.62 (br s, 1H); 8.60 (t, 1H); 7.72 (d, 1H); 7.66 (d, 1H); 6.94 (t, 1H); 4.03 (s, 3H); 3.31 (m, 2H); 2.19 (m, 1H); 1.14 (t, 3H); 0.83 (m, 2H); 0.60 (m, 2H);

Ex. no. 1-306: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.61 (br s, 1H); 8.67 (d, 1H); 7.72 (d, 1H); 7.65 (d, 1H); 6.94 (t, 1H); 4.03 (s, 3H); 2.84 (m, 1H); 2.16 (m, 1H); 0.83 (m, 2H); 0.70 (m, 2H); 0.57 (m, 4H);

Ex. no. 1-337: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.03 (br s, 1H); 7.98 (br s, 2H); 4.02 (s, 3H); 3.91 (br s, 1H); 2.07 (br s, 3H);

Ex. no. 1-338: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.22 (s, 1H); 8.00 (s, 1H); 7.97 (d, 1H); 7.94 (d, 1H); 4.03 (s, 3H);

Ex. no. 1-339: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.70 (d, 1H); 7.79 (d, 1H); 7.64 (d, 1H); 6.90 (t, 1H); 4.00 (s, 3H); 3.45 (m, 1H); 2.38 (s, 3H); 1.22 (d, 3H); 0.93 (m, 1H); 0.46 (m, 2H); 0.35 (m, 1H); 0.28 (m, 1H);

Ex. no. 1-340: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 8.79 (d, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 6.91 (t, 1H); 4.03 (s, 3H); 3.45 (m, 1H); 1.23 (d, 3H); 0.92 (m, 1H); 0.44 (m, 2H); 0.38 (m, 1H); 0.29 (m, 1H);

Ex. no. 1-341: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 8.66 (d, 1H); 7.83 (d, 1H); 7.76 (d, 1H); 4.01 (s, 3H); 3.40 (m, 1H); 2.84 (q, 2H); 2.78 (m, 1H); 1.22 (t, 3H); 1.17 (t, 3H); 0.91 (m, 1H); 0.43 (m, 2H); 0.29 (m, 2H);

Ex. no. 1-342: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.62 (q, 1H); 7.84 (d, 1H); 7.64 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-343: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.68 (t, 1H); 7.83 (d, 1H); 7.63 (d, 1H); 4.01 (s, 3H); 3.28 (q, 2H); 1.14 (t, 3H);

Ex. no. 1-344: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 8.74 (d, 1H); 7.82 (d, 1H); 7.63 (d, 1H); 4.01 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.56 (m, 2H);

Ex. no. 1-345: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.67 (t, 1H); 7.79 (d, 1H); 7.64 (d, 1H); 6.90 (t, 1H); 4.00 (s, 3H); 3.24 (m, 2H); 2.36 (s, 3H); 1.54 (m, 2H); 0.91 (t, 3H);

Ex. no. 1-346: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.57 (d, 1H); 7.79 (d, 1H); 7.63 (d, 1H); 6.91 (t, 1H); 4.11 (m, 1H); 4.00 (s, 3H); 2.36 (s, 3H); 1.16 (d, 6H);

Ex. no. 1-347: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.74 (t, 1H); 7.79 (d, 1H); 7.62 (d, 1H); 6.93 (t, 1H); 4.00 (s, 3H); 3.47 (m, 4H); 3.28 (s, 3H); 2.36 (s, 3H);

Ex. no. 1-348: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.81 (t, 1H); 7.80 (d, 1H); 7.65 (d, 1H); 7.01 (t, 1H); 4.00 (s, 3H); 3.49 (m, 2H); 2.68 (m, 2H); 2.38 (s, 3H); 2.11 (s, 3H);

Ex. no. 1-349: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.65 (q, 1H); 7.73 (d, 1H); 7.70 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H);

Ex. no. 1-350: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.71 (t, 1H); 7.73 (d, 1H); 7.69 (d, 1H); 4.01 (s, 3H); 3.28 (m, 2H); 1.14 (t, 3H);

Ex. no. 1-351: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 8.77 (d, 1H); 7.72 (d, 1H); 7.68 (d, 1H); 4.01 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.55 (m, 2H);

Ex. no. 1-352: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.56 (d, 1H); 7.94 (d, 1H); 7.86 (d, 1H); 4.06 (s, 3H); 3.47 (m, 1H); 2.45 (s, 3H); 1.21 (d, 3H); 0.91 (m, 1H); 0.41 (m, 2H); 0.33 (m, 2H);

Ex. no. 1-353: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.65 (d, 1H); 7.82 (br s, 2H); 6.88 (t, 1H); 4.05 (s, 3H); 3.51 (m, 1H); 2.44 (s, 3H); 1.23 (d, 3H); 0.93 (m, 1H); 0.41 (m, 3H); 0.30 (m, 1H);

Ex. no. 1-354: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.35 (q, 1H); 7.74 (d, 1H); 7.19 (d, 1H); 3.97 (s, 3H); 3.85 (s, 3H); 2.74 (d, 3H);

Ex. no. 1-355: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.64 (br s, 1H); 8.41 (t, 1H); 7.74 (d, 1H); 7.18 (d, 1H); 3.97 (s, 3H); 3.85 (s, 3H); 3.24 (m, 2H); 1.10 (t, 3H);

Ex. no. 1-356: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.64 (br s, 1H); 8.48 (d, 1H); 7.73 (d, 1H); 7.18 (d, 1H); 3.97 (s, 3H); 3.85 (s, 3H); 2.79 (m, 1H); 0.68 (m, 2H); 0.49 (m, 2H);

Ex. no. 1-357: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.05 (br s, 1H); 11.93 (br s, 1H); 8.06 (d, 1H); 7.99 (d, 1H); 4.02 (s, 3H); 3.74 (s, 3H);

Ex. no. 1-358: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.04 (br s, 1); 11.81 (br s, 1H); 8.05 (d, 1H); 7.99 (d, 1H); 4.02 (s, 3H); 3.97 (m, 2H); 1.23 (t, 3H);

Ex. no. 1-359: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.04 (br s, 1H); 11.81 (br s, 1H); 8.05 (d, 1H); 7.98 (d, 1H); 4.02 (s, 3H); 3.88 (m, 2H); 1.64 (m, 2H); 0.94 (t, 3H);

Ex. no. 1-360: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.04 (br s, 1H); 11.65 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.18 (m, 1H); 4.02 (s, 3H); 1.22 (d, 6H);

Ex. no. 1-361: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.98 (br s, 1H); 11.92 (br s, 1H); 7.98 (d, 1H); 7.81 (d, 1H); 7.04 (t, 1H); 4.01 (s, 3H); 3.76 (s, 3H);

Ex. no. 1-362: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.98 (br s, 1H); 11.81 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.02 (t, 1H); 4.01 (s, 3H); 3.99 (q, 2H); 1.23 (t, 3H);

Ex. no. 1-363: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.97 (br s, 1H); 11.81 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.02 (t, 1H); 4.01 (s, 3H); 3.90 (t, 2H); 1.64 (m, 2H); 0.94 (t, 3H);

Ex. no. 1-364: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.97 (br s, 1H); 11.67 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.21 (m, 1H); 4.01 (s, 3H); 1.23 (d, 6H);

Ex. no. 2-19: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 8.57 (q, 1H); 7.94 (d, 1H); 7.88 (d, 1H); 4.36 (q, 2H); 3.27 (s, 3H); 2.78 (d, 3H); 2.35 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-20: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 8.63 (t, 1H); 7.94 (d, 1H); 7.87 (d, 1H); 4.35 (q, 2H); 3.27 (m, 2H); 3.27 (s, 3H); 2.37 (s, 3H); 1.47 (t, 3H); 1.13 (t, 3H);

Ex. no. 2-21: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.70 (d, 1H); 7.93 (d, 1H); 7.87 (d, 1H); 4.35 (q, 2H); 3.27 (s, 3H); 2.77 (m, 1H); 2.35 (s, 3H); 1.47 (t, 3H); 0.69 (m, 2H); 0.62 (m, 1H); 0.51 (m, 1H);

Ex. no. 2-25: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.51 (q, 1H) 7.82 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 2.79 (d, 3H); 2.33 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-26: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.60 (t, 1H); 7.83 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 3.30 (m, 2H); 2.35 (s, 3H); 1.47 (t, 3H); 1.11 (t, 3H);

Ex. no. 2-27: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.64 (br s, 1H); 8.66 (d, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 4.35 (q, 2H); 2.81 (m, 1H); 2.34 (s, 3H); 1.47 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 2-28: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.68 (br s, 1H); 8.72 (t, 1H); 7.82 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 3.13 (m, 2H); 2.38 (s, 3H); 1.47 (t, 3H); 1.01 (m, 1H); 0.45 (m, 2H); 0.23 (m, 2H);

Ex. no. 2-29: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 9.38 (t, 1H); 7.87 (d, 1H); 7.80 (d, 1H); 4.35 (q, 2H); 4.13 (m, 2H); 2.35 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-30: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.68 (br s, 1H); 9.08 (t, 1H); 7.85 (d, 1H); 7.78 (d, 1H); 6.14 (tt, 1H); 4.35 (q, 2H); 3.70 (m, 2H); 2.36 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-31: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.66 (br s, 1H); 0.62 (t, 1H); 7.81 (d, 1H); 7.75 (d, 1H); 4.35 (q, 2H); 3.40 (m, 1H); 2.39 (d, 3H); 1.48 (t, 3H); 1.20 (dd, 3H); 0.90 (m, 1H); 0.45 (m, 2H); 0.30 (m, 2H);

Ex. no. 2-32: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.67 (br s, 1H); 8.62 (t, 1H); 7.82 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 3.21 (m, 2H); 2.36 (s, 3H); 1.51 (m, 2H); 1.47 (t, 3H); 0.91 (t, 3H);

Ex. no. 2-33: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.50 (d, 1H); 7.81 (d, 1H); 7.75 (d, 1H); 4.35 (q, 2H); 4.09 (m, 1H); 2.36 (s, 3H); 1.47 (t, 3H); 1.16 (d, 3H); 1.12 (d, 3H);

Ex. no. 2-34: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.66 (br s, 1H); 8.70 (d, 1H); 4.35 (q, 2H); 3.52-3.30 (m, 4H); 3.27 (s, 3H); 2.36 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-35: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.78 (t, 1H); 7.83 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 3.50 (m, 1H); 3.40 (m, 1H); 2.64 (m, 2H); 2.39 (s, 3H); 2.11 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-36: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 9.42 (t, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 4.49 (m, 2H); 4.36 (q, 2H); 2.35 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-37: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.67 (br s, 1H); 8.72 (br s, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 4.37 (q, 2H); 3.96 (m, 1H); 3.77 (m, 1H); 3.62 (m, 1H); 3.37 (m, 1H); 3.27 (m, 1H); 2.36 (s, 3H); 1.94 (m, 1H); 1.82 (m, 2H); 1.60 (m, 1H); 1.47 (t, 3H);

Ex. no. 2-42: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.66 (br s, 1H); 8.85 (d, 1H); 7.82 (d, 1H); 7.76 (d, 1H); 4.37 (m, 1H); 4.35 (q, 2H); 2.34 (s, 3H); 2.24 (m 2H); 1.97 (m, 2H); 1.69 (m, 2H); 1.47 (t, 3H);

Ex. no. 2-44: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.56 (q, 1H); 7.79 (d, 1H); 7.64 (d, 1H); 6.91 (t, 1H); 4.34 (q, 2H); 2.81 (d, 3H); 2.33 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-45: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.65 (t, 1H); 7.78 (d, 1H); 7.64 (d, 1H); 6.91 (t, 1H); 4.34 (q, 2H); 3.31 (m, 2H); 2.35 (s, 3H); 1.47 (t, 3H); 1.13 (t, 3H);

Ex. no. 2-46: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.71 (d, 1H); 7.78 (d, 1H); 7.63 (d, 1H); 6.91 (t, 1H); 4.34 (q, 2H); 2.85 (m, 1H); 2.33 (s, 3H); 1.47 (t, 3H); 0.71 (m, 2H); 0.53 (m, 2H);

Ex. no. 2-47: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.59 (br s, 1H); 8.79 (t, 1H); 7.79 (d, 1H); 7.64 (d, 1H); 6.92 (t, 1H); 4.35 (q, 2H); 3.16 (m, 2H); 2.38 (s, 3H); 1.47 (t, 3H); 1.05 (m, 1H); 0.46 (m, 2H); 0.24 (m, 2H);

Ex. no. 2-49: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.60 (br s, 1H); 9.12 (t, 1H); 7.82 (d, 1H); 7.66 (d, 1H); 6.93 (t, 1H); 6.19 (tt, 1H); 4.35 (q, 2H); 3.72 (m, 2H); 2.36 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-56: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.56 (br s, 1H); 8.53 (q, 1H); 7.88 (d, 1H); 7.67 (d, 1H); 4.34 (q, 2H); 3.86 (s, 3H); 2.79 (d, 3H); 1.47 (t, 3H);

Ex. no. 2-57: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.54 (br s, 1H); 8.61 (t, 1H); 7.88 (d, 1H); 7.67 (d, 1H); 4.34 (q, 2H); 3.88 (s, 3H); 3.28 (m, 2H); 1.47 (t, 3H); 1.11 (t, 3H);

Ex. no. 2-58: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.54 (br s, 1H); 8.68 (d, 1H); 7.87 (d, 1H); 7.66 (d, 1H); 4.34 (q, 2H); 3.87 (s, 3H); 2.80 (m, 1H); 1.47 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 2-72: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.42 (br s, 1H); 8.58 (q, 1H); 7.84 (d, 1H); 7.54 (d, 1H); 6.96 (t, 1H); 4.34 (q, 2H); 3.85 (s, 3H); 2.81 (d, 3H); 1.47 (t, 3H);

Ex. no. 2-73: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.42 (br s, 1H); 8.65 (t, 1H); 7.84 (d, 1H); 7.54 (d, 1H); 6.96 (t, 1H); 4.34 (q, 2H); 3.86 (s, 3H); 3.30 (m, 2H); 1.47 (t, 3H); 1.13 (t, 3H);

Ex. no. 2-74: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.40 (br s, 1H); 8.72 (d, 1H); 7.83 (d, 1H); 7.53 (d, 1H); 6.95 (t, 1H); 4.33 (q, 2H); 3.85 (s, 3H); 2.85 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.55 (m, 2H);

Ex. no. 2-81: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 8.48 (q, 1H); 7.95 (d, 1H); 7.86 (d, 1H); 4.43 (q, 2H); 2.80 (d, 3H); 2.43 (s, 3H); 1.48 (t, 3H);

Ex. no. 2-82: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.70 (br s, 1H); 8.56 (t, 1H); 7.94 (d, 1H); 7.86 (d, 1H); 4.43 (q, 2H); 3.30 (m, 2H); 2.44 (s, 3H); 1.48 (t, 3H); 1.13 (s, 3H);

Ex. no. 2-83: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.72 (br s, 1H); 8.64 (d, 1H); 7.94 (d, 1H); 7.86 (d, 1H); 4.43 (q, 2H); 2.80 (m, 1H); 2.43 (s, 3H); 1.48 (t, 3H); 0.71 (m, 2H); 0.53 (br s, 2H);

Ex. no. 2-84: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 8.68 (t, 1H); 7.95 (d, 1H); 7.86 (d, 1H); 4.44 (q, 2H); 3.16 (m, 2H); 2.45 (s, 3H); 1.47 (t, 3H); 1.02 (m, 1H); 0.45 (m, 2H); 0.25 (m, 2H);

Ex. no. 2-86: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.73 (br s, 1H); 9.10 (t, 1H); 7.98 (d, 1H); 7.91 (d, 1H); 6.12 (tt, 1H); 4.43 (q, 2H); 3.71 (m, 2H); 2.43 (s, 3H); 1.49 (t, 3H);

Ex. no. 2-87: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.55 (q, 1H); 7.81 (s, 2H); 6.91 (t, 1H); 4.43 (q, 2H); 2.83 (d, 3H); 2.42 (s. 3H); 1.49 (t 3H);

Ex. no. 2-88: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.62 (t, 1H); 7.81 (s, 2H); 6.90 (t, 1H); 4.43 (q, 2H); 3.32 (m, 2H); 2.43 (s, 3H); 1.48 (t, 3H); 1.15 (t, 3H);

Ex. no. 2-89: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.70 (d, 1H); 7.80 (br s, 2H); 6.90 (t, 1H); 4.43 (q, 2H); 2.85 (m, 1H); 2.41 (s, 3H); 1.48 (t, 3H); 0.72 (m, 2H); 0.57 (m, 2H);

Ex. no. 2-90: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.66 (br s, 1H); 8.76 (t, 1H); 7.83 (m, 2H); 6.91 (t, 1H); 4.43 (q, 2H); 3.19 (m, 2H); 2.44 (s, 3H); 1.49 (t, 3H); 1.06 (m, 1H); 0.46 (m, 2H); 0.26 (m, 2H);

Ex. no. 2-92: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.68 (br s, 1H); 9.14 (t, 1H); 7.84 (br s, 2H); 6.92 (t, 1H); 6.18 (tt, 1H); 4.43 (q, 2H); 3.73 (m, 2H); 2.42 (s, 3H); 1.48 (t, 3H);

Ex. no. 2-123: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.92 (br s, 1H); 8.73 (q, 1H); 8.07 (d, 1H); 8.02 (d, 1H); 4.37 (q, 2H); 2.79 (d, 3H); 1.47 (t, 3H);

Ex. no. 2-125: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.85 (d, 1H); 8.05 (d, 1H); 8.02 (d, 1H); 4.37 (q, 2H); 3.31 (s, 3H); 2.77 (m, 1H); 1.47 (t, 3H); 0.69 (m, 2H); 0.58 (m, 2H);

Ex. no. 2-129: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.70 (q, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.37 (q, 2H); 2.79 (d, 3H); 1.47 (t, 3H);

Ex. no. 2-130: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.76 (t, 1H); 7.96 (d, 1H); 7.93 (d, 1H); 4.37 (q, 2H); 3.28 (m, 2H); 1.47 (t, 3H); 1.12 (t, 3H);

Ex. no. 2-131: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.83 (d, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.37 (q, 2H); 2.80 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.50 (br s, 2H);

Ex. no. 2-132: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.89 (t, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.38 (q, 2H); 3.15 (m, 3H); 1.47 (t, 3H); 0.46 (m, 2H); 0.23 (m, 2H);

Ex. no. 2-133: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.96 (br s, 1H); 9.56 (t, 1H); 8.03 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 4.15 (m, 2H); 1.47 (t, 3H);

Ex. no. 2-134: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 9.29 (t, 1H); 8.01 (d, 1H); 7.96 (d, 1H); 6.12 (tt, 1H); 4.38 (q, 2H); 3.71 (m, 2H); 1.47 (t, 3H);

Ex. no. 2-135: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.77 (d, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.38 (q, 2H); 3.43 (m, 1H); 1.48 (t, 3H); 1.20 (m, 3H); 0.90 (m, 1H); 0.43 (m, 2H); 0.30 (m, 2H);

Ex. no. 2-138: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 8.91 (t, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.38 (q, 2H); 3.45 (m, 4H); 3.27 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-139: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.99 (t, 1H); 7.98 (d, 1H); 7.93 (d, 1H); 4.38 (q, 2H); 3.45 (m, 2H); 2.63 (t, 2H); 2.11 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-141: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 8.90 (t, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.37 (q, 2H); 3.96 (m, 1H); 3.78 (m, 1H); 3.65 (m, 1H); 3.32 (br s, 2H); 1.93 (m, 1H); 1.83 (m, 2H); 1.62 (m, 1H); 1.47 (t, 3H);

Ex. no. 2-142: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.90 (t, 1H); 7.95 (d, 1H); 7.90 (d, 1H); 4.37 (q, 2H); 4.18 (br d, 2H); 3.00 (s, 3H); 2.86 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-143: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.98 (br s, 1H); 10.88 (br s, 1H); 8.06 (d, 1H); 8.02 (d, 1H); 7.65 (d, 2H); 7.38 (t, 2H); 7.16 (t, 1H); 4.38 (q, 2H); 1.47 (t, 3H);

Ex. no. 2-144: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 9.37 (t, 1H); 7.98 (d, 1H); 7.93 (d, 1H); 7.45 (m, 1H); 7.07 (m, 1H); 6.99 (m, 1H); 4.66 (br s, 2H); 4.37 (q, 2H); 1.47 (t, 3H);

Ex. no. 2-146: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.61 (br s, 1H); 7.74 (d, 1H); 7.71 (d, 1H); 4.62 (m, 1H); 4.57 (q, 2H); 2.46 (m, 2H); 2.19 (m, 2H); 1.82 (m, 2H); 1.62 (t, 3H);

Ex. no. 2-147: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.83 (br s, 1H); 8.72 (q, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.37 (q, 2H); 2.81 (d, 3H); 1.47 (t, 3H);

Ex. no. 2-148: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.79 (t, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.37 (q, 2H); 3.31 (m, 2H); 1.47 (t, 3H); 1.13 (t, 3H);

Ex. no. 2-149: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.85 (d, 1H); 7.89 (d, 1H); 7.77 (d, 1H); 6.95 (t, 1H); 4.37 (q, 2H); 2.84 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.55 (m, 2H);

Ex. no. 2-154: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.84 (br s, 1H); 8.81 (t, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.95 (t, 1H); 4.37 (q, 2H); 3.24 (m, 2H); 1.54 (m, 2H); 1.47 (t, 3H); 0.92 (t, 3H);

Ex. no. 2-155: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.83 (br s, 1H); 8.70 (d, 1H); 7.89 (d, 1H); 7.77 (d, 1H); 6.95 (t, 1H); 4.37 (q, 2H); 4.09 (m, 1H); 1.47 (t, 3H); 1.16 (d, 6H);

Ex. no. 2-156: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.84 (br s, 1H); 8.93 (t, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.93 (t, 1H); 4.37 (q, 2H); 3.47 (m, 4H); 3.29 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-157: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.85 (br s, 1H); 8.99 (t, 1H); 7.92 (d, 1H); 7.80 (d, 1H); 7.05 (t, 1H); 4.37 (q, 2H); 3.49 (m, 2H); 2.67 (m, 2H); 2.12 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-158: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 9.59 (t, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.37 (m, 4H); 1.47 (t, 3H);

Ex. no. 2-159: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.84 (br s, 1H); 8.94 (t, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.98 (t, 1H); 4.37 (q, 2H); 3.99 (m, 1H); 3.78 (m, 1H); 3.65 (m, 1H); 3.35 (m, 2H); 1.94 (m, 1H); 1.84 (m, 2H); 1.62 (m, 1H); 1.47 (t, 3H);

Ex. no. 2-160: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.84 (br s, 1H); 9.12 (t, 1H); 7.93 (d, 1H); 7.83 (d, 1H); 7.58 (t, 1H); 4.37 (q, 2H); 4.17 (d, 2H); 3.02 (s, 3H); 2.89 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-161: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 10.84 (br s, 1H); 7.98 (d, 1H); 7.85 (d, 1H); 7.69 (m, 2H); 7.38 (m, 2H); 7.16 (m, 1H); 7.12 (t, 1H); 4.38 (q, 2H); 1.48 (t, 3H);

Ex. no. 2-162: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.85 (br s, 1H); 9.45 (t, 1H); 7.92 (d, 1H); 7.79 (d, 1H); 7.45 (m, 1H); 7.07 (m, 1H); 6.99 (m, 1H); 6.92 (t, 1H); 4.68 (d, 2H); 4.36 (q, 2H); 1.47 (t, 3H);

Ex. no. 2-164: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.84 (br s, 1H); 9.05 (d, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.93 (t, 1H); 4.37 (m, 3H); 2.25 (m, 2H); 2.01 (m, 2H); 1.71 (m, 2H); 1.47 (t, 3H);

Ex. no. 2-173: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.79 (d, 1H); 7.76 (d, 1H); 7.66 (d, 1H); 4.35 (q, 2H); 2.82 (m, 1H); 1.47 (t, 3H); 0.73 (m, 2H); 0.53 (m, 2H);

Ex. no. 2-177: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 8.65 (d, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 4.35 (q, 2H); 2.79 (d, 3H); 1.46 (t, 3H);

Ex. no. 2-178: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 8.71 (t, 1H); 7.81 (d, 1H); 7.67 (d, 1H); 4.35 (q, 1H); 3.28 (m, 2H); 1.46 (t, 3H); 1.14 (t, 3H);

Ex. no. 2-179: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.77 (d, 1H); 7.80 (d, 1H); 7.67 (d, 1H); 4.35 (q, 2H); 2.81 (m, 1H); 1.46 (t, 3H); 0.72 (m, 2H); 0.54 (m, 2H);

Ex. no. 2-180: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 8.80 (t, 1H); 7.81 (d, 1H); 7.67 (d, 1H); 4.35 (q, 2H); 3.16 (m, 2H); 1.46 (t, 3H); 1.02 (m, 1H); 0.46 (m, 2H); 0.26 (m, 2H);

Ex. no. 2-181: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.81 (br s, 1H); 9.50 (t, 1H); 7.85 (d, 1H); 7.73 (d, 1H); 4.35 (q, 2H); 4.13 (m, 2H); 1.46 (t, 3H);

Ex. no. 2-182: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 9.23 (t, 1H); 7.83 (d, 1H); 7.71 (d, 1H); 6.14 (tt, 1H); 4.35 (q, 2H); 3.70 (m, 2H); 1.46 (t, 3H);

Ex. no. 2-183: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.79 (br s, 1H); 8.67 (d, 1H); 7.80 (d, 1H); 7.66 (d, 1H); 4.35 (q, 2H); 3.49 (m, 1H); 1.47 (t, 3H); 1.22 (d, 3H); 0.92 (m, 1H); 0.43 (m, 2H); 0.32 (m, 2H);

Ex. no. 2-184: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.72 (t, 1H); 7.81 (d, 1H); 7.67 (d, 1H); 4.35 (q, 2H); 3.22 (m, 2H); 1.56 (m, 2H); 1.46 (t, 3H); 0.94 (t, 3H);

Ex. no. 2-185: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.77 (br s, 1H); 7.80 (d, 1H); 7.66 (d, 1H); 4.35 (q, 2H); 4.06 (m, 1H); 1.46 (t, 3H); 1.17 (d, 6H);

Ex. no. 2-186: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.78 (br s, 1H); 8.86 (t, 1H); 7.80 (d, 1H); 7.67 (d, 1H); 4.35 (q, 2H); 3.48 (m, 2H); 3.41 (m, 2H); 3.28 (s, 3H); 1.46 (s, 3H);

Ex. no. 2-187: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.80 (br s, 1H); 8.93 (t, 1H); 7.81 (d, 1H); 7.69 (d, 1H); 4.35 (q, 2H); 3.44 (m, 2H); 2.67 (m, 2H); 2.09 (s, 3H); 1.46 (t, 3H);

Ex. no. 2-195: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.74 (br s, 1H); 8.58 (q, 1H); 7.98 (d, 1H); 7.46 (d, 1H); 4.34 (q, 2H); 2.79 (d, 3H); 1.45 (t, 3H);

Ex. no. 2-196: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.75 (br s, 1H); 8.64 (t, 1H); 7.98 (d, 1H); 7.46 (d, 1H); 4.34 (q, 2H); 3.27 (m, 2H); 1.46 (t, 3H); 1.15 (t, 3H);

Ex. no. 2-197: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.72 (br s, 1H); 8.70 (d, 1H); 7.97 (d, 1H); 7.45 (d, 1H); 4.34 (q, 2H); 2.79 (m, 1H); 1.45 (t, 3H); 0.72 (m, 2H); 0.57 (br s, 2H);

Ex. no. 2-207: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.67 (q, 1H); 7.96 (d, 1H); 7.91 (d, 1H); 4.39 (q, 2H); 2.79 (d, 3H); 1.48 (t, 3H);

Ex. no. 2-208: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.73 (t, 1H); 7.95 (d, 1H); 7.90 (d, 1H); 4.39 (q, 2H); 3.29 (m, 2H); 1.48 (t, 3H); 1.12 (t, 3H);

Ex. no. 2-210: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.84 (t, 1H); 7.96 (d, 1H); 7.90 (d, 1H); 4.40 (q, 2H); 3.14 (m, 2H); 1.48 (t, 3H); 1.01 (m, 1H); 0.46 (m, 2H); 0.24 (m, 2H);

Ex. no. 2-211: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 9.52 (t, 1H); 8.00 (d, 1H); 7.96 (d, 1H); 4.40 (q, 2H); 4.19 (m, 1H); 4.08 (m, 1H); 1.48 (t, 3H);

Ex. no. 2-212: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 9.26 (t, 1H); 7.99 (d, 2H); 7.94 (d, 1H); 6.12 (tt, 1H); 4.40 (q, 2H); 3.70 (m, 2H); 1.48 (t, 3H);

Ex. no. 2-213: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 8.73 (t, 1H); 7.95 (d, 1H); 4.40 (q, 2H); 3.42 (m, 1H); 1.48 (t, 3H); 1.24 and 1.18 (2x d, 3H); 0.90 (m, 1H); 0.33 (m, 4H);

Ex. no. 2-225: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.70 (q, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 6.94 (t, 1H); 4.39 (q, 2H); 2.81 (d, 3H); 1.47 (t, 3H);

Ex. no. 2-226: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.77 (t, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.39 (q, 2H); 3.30 (m, 2H); 1.48 (t, 3H); 1.14 (t, 3H);

Ex. no. 2-227: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.81 (br s, 1H); 8.83 (d, 1H); 7.84 (d, 1H); 7.80 (d, 1H); 6.93 (t, 1H); 4.39 (q, 2H); 2.83 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.57 (m, 2H);

Ex. no. 2-228: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 8.90 t, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.39 (q, 2H); 3.16 (t, 2H); 1.48 (t, 3H); 1.04 (m, 1H); 0.48 (m, 2H); 0.25 (m, 2H);

Ex. no. 2-229: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.84 (br s, 1H); 9.54 (t, 1H); 7.90 (d, 1H); 7.84 (d, 1H); 6.93 (t, 1H); 4.39 (q, 2H); 4.14 (m, 2H); 1.48 (t, 3H);

Ex. no. 2-230: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.83 (br s, 1H); 9.28 (t, 1H); 7.89 (d, 1H); 7.83 (d, 1H); 6.94 (t, 1H); 6.18 (tt, 1H); 4.39 (q, 2H); 3.72 (m, 2H); 1.48 (t, 3H);

Ex. no. 2-271: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.53 (q, 1H); 7.84 (d, 1H); 7.77 (d, 1H); 4.36 (q, 2H); 2.79 (d, 3H); 2.69 (m, 2H); 1.48 (t, 3H); 1.17 (t, 3H);

Ex. no. 2-272: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.69 (br s, 1H); 8.62 (t, 1H); 7.83 (d, 1H); 7.77 (d, 1H); 4.36 (q, 2H); 3.29 (m, 2H); 2.77 (m, 2H); 1.48 (t, 3H); 1.18 (t, 3H); 1.11 (t, 3H);

Ex. no. 2-273: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.67 (br s, 1H); 8.67 (d, 1H); 7.82 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 2.80 (m, 2H); 2.70 (m, 1H); 1.47 (t, 3H); 1.17 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 2-276: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 9.10 (t, 1H); 7.86 (d, 1H); 7.79 (d, 1H); 6.13 (tt, 1H); 4.36 (q, 2H); 3.78 (m, 1H); 3.63 (m, 1H); 2.77 (m, 2H); 1.48 (t, 3H); 1.17 (t, 3H);

Ex. no. 2-277: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.62 (br s, 1H); 8.58 (q, 1H); 7.79 (d, 1H); 7.65 (d, 1H); 6.90 (t, 1H); 4.35 (q, 2H); 2.81 (d, 3H); 2.74 (q, 2H); 1.47 (t, 3H); 1.15 (t, 3H);

Ex. no. 2-278: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.61 (br s, 1H); 8.67 (t, 1H); 7.79 (d, 1H); 7.65 (d, 1H); 6.90 (t, 1H); 4.35 (q, 2H); 3.31 (m, 2H); 2.76 (q, 2H); 1.48 (t, 3H); 1.15 (2x t, 6H);

Ex. no. 2-279: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.60 (br s, 1H); 8.74 (d, 1H); 7.78 (d, 1H); 7.64 (d, 1H); 6.89 (t, 1H); 4.35 (q, 2H); 2.86 (m, 1H); 2.73 (m, 2H); 1.47 (t, 3H); 1.15 (t, 3H); 0.72 (m, 2H); 0.53 (m, 2H);

Ex. no. 2-286: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.59 (br s, 1H); 8.45 (q, 1H); 7.77 (br s, 2H); 4.38 (q, 2H); 2.79 (d, 3H); 2.11 (m, 1H); 1.48 (t, 3H); 0.84 (m, 2H); 0.64 (m, 2H);

Ex. no. 2-287: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.51 (t, 1H); 7.77 (br s, 2H); 4.38 (q, 2H); 3.29 (m, 2H); 2.14 (m, 1H); 1.48 (t, 3H); 1.13 (t, 3H); 0.84 (m, 2H); 0.67 (m, 2H);

Ex. no. 2-288: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.59 (d, 1H); 7.76 (br s, 2H); 4.37 (q, 2H); 2.79 (m, 1H); 2.12 (m, 1H); 1.48 (t, 3H); 0.85 (m, 2H); 0.70 (m, 2H); 0.66 (m, 2H); 0.51 (br s, 2H);

Ex. no. 2-289: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.64 (t, 1H); 7.77 (br s, 2H); 4.38 (q, 2H); 3.13 (m, 2H); 2.15 (m, 1H); 1.49 (t, 3H); 1.03 (m, 1H); 0.86 (m, 2H); 0.68 (m, 2H); 0.45 (m, 2H); 0.23 (m, 2H);

Ex. no. 2-291: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.60 (br s, 1H); 9.03 (t, 1H); 7.80 (br s, 2H); 6.13 (tt, 1H); 4.38 (q, 2H); 3.69 (m, 2H); 2.13 (m, 1H); 1.49 (t, 3H); 0.87 (m, 2H); 0.65 (m, 2H);

Ex. no. 2-292: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.55 (d, 1H); 7.76 (br s, 2H); 4.38 (q, 2H); 3.37 (m, 1H); 2.17 (m, 1H); 1.49 (t, 3H); 1.20 (br s, 3H); 0.89 (m, 3H); 0.70 (br s, 2H); 0.45 (m, 2H); 0.24 (m, 1H);

Ex. no. 2-304: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.52 (br s, 1H); 8.53 (q, 1H); 7.72 (d, 1H); 7.66 (d, 1H); 6.94 (t, 1H); 4.37 (q, 2H); 2.81 (d, 3H); 2.16 (m, 1H); 1.49 (t, 3H); 0.83 (m, 2H); 0.58 (m, 2H);

Ex. no. 2-305: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.52 (br s, 1H); 8.61 (t, 1H); 7.72 (d, 1H); 7.66 (d, 1H); 6.95 (t, 1H); 4.38 (q, 2H); 2.32 (q, 2H); 2.19 (m, 1H); 1.49 (t, 3H); 1.14 (3H); 0.83 (m, 2H); 0.61 (m, 2H);

Ex. no. 2-306: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.51 (br s, 1H); 8.68 (d, 1H); 7.72 (d, 1H); 7.65 (d, 1H); 6.94 (t, 1H); 4.37 (q, 2H); 2.85 (m, 1H); 2.16 (m, 1H); 1.48 (t, 3H); 0.83 (m, 2H); 0.71 (m, 2H); 0.58 (m, 4H);

Ex. no. 2-337: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 7.98 (br s, 2H); 4.37 (q, 2H); 3.81 (br s, 1H); 2.07 (br s, 3H); 1.47 (t, 3H);

Ex. no. 2-338: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 8.22 (s, 1H); 8.00 (s, 1H); 7.96 (d, 1H); 7.93 (d, 1); 4.39 (q, 2H); 1.49 (t, 3H);

Ex. no. 2-339: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.59 (br s, 1H); 8.70 (d, 1H); 7.78 (d, 1H); 7.64 (d, 1H); 6.91 (t, 1H); 4.35 (q, 2H); 3.45 (m, 1H); 2.38 (s, 3H); 1.47 (t, 3H); 1.22 (d, 3H); 0.93 (m, 1H); 0.45 (m, 2H); 0.35 (m, 1H); 0.27 (m, 1H);

Ex. no. 2-340: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.81 (br s, 1H); 8.79 (d, 1H); 7.84 (d, 1H); 7.81 (d, 1H); 6.91 (t, 1H); 4.39 (q, 2H); 3.45 (m, 1H); 1.48 (s, 3H); 1.23 (d, 3H); 0.93 (m, 1H); 0.44 (m, 2H); 0.38 (m, 1H); 0.29 (m, 1H);

Ex. no. 2-341: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.68 (br s, 1H); 8.67 (d, 1H); 7.82 (d, 1H); 7.76 (d, 1H); 4.36 (q, 2H); 3.40 (m, 1H); 2.82 (q, 2H); 2.78 (m, 1H); 1.48 (t, 3H); 1.22 (t, 3H); 1.19 (t, 3H); 0.91 (m, 1H); 0.45 (m, 2H); 0.29 (m, 2H);

Ex. no. 2-342: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.68 (t, 1H); 7.83 (d, 1H); 7.62 (d, 1H); 4.37 (q, 2H); 3.28 (m, 2H); 1.47 (s, 3H); 1.14 (t, 3H);

Ex. no. 2-343: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.75 (br s, 1H); 8.74 (d, 1H); 7.82 (d, 1H); 7.61 (d, 1H); 4.37 (q, 2H); 2.79 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.56 (m, 2H);

Ex. no. 2-344: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.59 (br s, 1H); 8.67 (t, 1H); 7.79 (d, 1H); 7.64 (d, 1H); 6.90 (t, 1H); 4.35 (q, 2H); 3.24 (m, 2H); 2.35 (s, 3H); 1.54 (m, 2H); 1.47 (t, 3H); 0.92 (t, 3H);

Ex. no. 2-345: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.58 (br s, 1H); 8.56 (d, 1H); 7.78 (d, 1H); 7.63 (d, 1H); 6.91 (t, 1H); 4.34 (q, 2H); 4.11 (m, 1H); 2.36 (s, 3H); 1.47 (t, 3H); 1.16 (d, 6H);

Ex. no. 2-346: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.59 (br s, 1H); 8.74 (t, 1H); 7.78 (d, 1H); 7.64 (d, 1H); 6.93 (t, 1H); 4.35 (q, 2H); 3.47 (m, 4H); 3.28 (s, 3H); 2.35 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-347: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.59 (br s, 1H); 8.81 (t, 1H); 7.79 (d, 1H); 7.65 (d, 1H); 7.01 (t, 1H); 4.35 (q, 2H); 3.49 (m, 2H); 2.68 (m, 2H); 2.38 (s, 3H); 2.11 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-348: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.77 (br s, 1H); 8.71 (t, 1H); 7.72 (d, 1H); 7.69 (d, 1H); 4.37 (q, 2H); 3.28 (m, 2H); 1.47 (t, 3H); 1.14 (t, 3H);

Ex. no. 2-349: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.76 (br s, 1H); 8.77 (d, 1H); 7.71 (d, 1H); 7.68 (d, 1H); 4.37 (q, 2H); 2.80 (m, 2H); 1.47 (t, 3H); 0.72 (m, 2H); 0.54 (m, 2H);

Ex. no. 2-350: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.71 (br s, 1H); 8.57 (d, 1H); 7.94 (d, 1H); 7.85 (d, 1H); 4.44 (q, 2H); 3.47 (m, 1H); 2.46 (s, 3H); 1.49 (t, 3H); 1.21 (d, 3H); 0.91 (m, 1H); 0.42 (m, 2H); 0.33 (m, 2H);

Ex. no. 2-351: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.66 (d, 1H); 7.83 (d, 1H); 7.79 (d, 1H); 6.89 (t, 1H); 4.44 (q, 2H); 3.51 (m, 1H); 2.45 (s, 3H); 1.49 (t, 3H); 1.23 (d, 3H); 0.93 (m, 1H); 0.30 (m, 2H);

Ex. no. 2-352: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.54 (br s, 1H); 8.35 (q, 1H); 7.73 (d, 1H); 7.19 (d, 1H); 7.33 (m, 2H); 3.85 (s, 3H); 2.74 (d, 3H); 1.45 (t, 3H);

Ex. no. 2-353: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.53 (br s, 1H); 8.41 (t, 1H); 7.72 (d, 1H); 7.18 (d, 1H); 4.33 (q, 2H); 3.85 (s, 3H); 3.24 (m, 2H); 1.46 (t, 3H); 1.10 (t, 3H);

Ex. no. 2-354: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.53 (br s, 1H); 8.48 (d, 1H); 7.72 (d, 1H); 7.18 (d, 1H); 4.33 (q, 2H); 3.85 (s, 3H); 2.80 (m, 1H); 1.47 (t, 3H); 0.69 (m, 2H); 0.48 (m, 2H);

Ex. no. 2-357: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 11.93 (br s, 1H); 8.05 (d, 1H); 7.99 (d, 1H); 4.38 (q, 2H); 3.74 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-358: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.94 (br s, 1H); 11.81 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 3.97 (m, 2H); 1.48 (t, 3H); 1.23 (t, 3H);

Ex. no. 2-359: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 11.81 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 3.88 (m, 2H); 1.64 (m, 2H); 1.47 (t, 3H); 0.94 (t, 3H);

Ex. no. 2-360: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.93 (br s, 1H); 11.65 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 4.18 (m, 2H); 1.47 (t, 3H); 1.23 (d, 6H);

Ex. no. 2-361: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.92 (br s, 1H); 11.87 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.04 (t, 1H); 4.37 (q, 2H); 3.76 (s, 3H); 1.47 (t, 3H);

Ex. no. 2-362: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 11.81 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.02 (t, 1H); 4.37 (q, 2H); 3.99 (q, 2H); 1.47 (t, 3H); 1.23 (t, 3H);

Ex. no. 2-363: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 11.81 (br s, 1H); 7.96 (d, 1H); 7.81 (d, 1H); 7.02 (t, 1H); 4.38 (q, 2H); 3.91 (t, 2H); 1.65 (m, 2H); 1.48 (t, 3H); 0.95 (t, 3H);

Ex. no. 2-364: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.87 (br s, 1H); 11.67 (br s, 1H); 7.96 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.37 (q, 2H); 4.21 (m, 1H); 1.47 (t, 3H); 1.23 (d, 6H);

Ex. no. 3-26: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.63 (br s, 1H); 8.59 (t, 1H); 7.80 (d, 1H); 7.76 (d, 1H); 4.30 (t, 2H); 3.28 (m, 2H); 2.35 (s, 3H); 1.88 (m, 2H); 1.11 (t, 3H); 0.88 (t, 3H);

Ex. no. 3-27: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.62 (br s, 1H); 8.66 (d, 1H); 7.80 (d, 1H); 7.75 (d, 1H); 4.30 (t, 2H); 2.81 (m, 1H); 2.34 (s, 3H); 1.88 (m, 2H); 0.88 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 3-125: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.90 (br s, 1H); 8.85 (d, 1H); 8.06 (d, 1H); 8.00 (d, 1H); 4.32 (t, 2H); 3.31 (s, 3H); 2.77 (m, 1H); 1.88 (m, 2H); 0.88 (t, 3H); 0.70 (m, 2H); 0.58 (m, 2H);

Ex. no. 3-129: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.88 (br s, 1H); 8.70 (q, 1 h); 7.96 (d, 1H); 7.93 (d, 1H); 4.32 (t, 2H); 2.80 (d, 3H); 1.88 (m, 2H); 0.88 (t, 3H);

Ex. no. 3-208: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.85 (br s, 1H); 8.73 (t, 1H); 7.95 (d, 1H); 7.89 (d, 1H); 4.34 (t, 2H); 3.29 (m, 2H); 1.89 (m 2H); 1.12 (t, 3H); 0.89 (t, 3H);

Ex. no. 3-273: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.65 (br s, 1H); 8.68 (d, 1H); 7.81 (d, 1H); 7.76 (d, 1H); 4.30 (t, 2H); 2.81 (m 2H); 2.70 (m, 1H); 1.89 (m, 2H); 1.17 (t, 3H); 0.89 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Ex. no. 3-337: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.91 (br s, 1H); 7.97 (br s, 2H); 4.31 (t, 2H); 3.89 (br s, 1H); 2.07 (br s, 3H); 1.89 (m, 2H); 0.88 (t, 3H);

Ex. no. 3-338: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.89 (br s, 1H); 8.22 (s, 1H); 8.01 (s, 1H); 7.94 (s, 2H); 4.34 (t, 2H); 1.90 (m, 2H); 0-90 (t, 3H);

Ex. no. 4-212: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.22 (br s, 1H); 8.66 (d, 1H); 7.91 (s, 1H); 7.77 (d, 1H); 7.72 (d, 1H); 3.77 (s, 3H); 2.80 (m, 2H); 2.71 (m, 1H); 1.17 (t, 3H); 0.71 (m, 2H); 0.48 (m, 2H);

Ex. no. 5-58: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.45 (br s, 1H); 9.05 (s, 1H); 8.46 (q, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 2.79 (d, 3H); 2.39 (s, 3H);

Ex. no. 5-59: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.42 (br s, 1H); 9.07 (s, 1H); 8.53 (t, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 3.28 (m, 2H); 2.40 (s, 3H); 1.12 (t, 3H);

Ex. no. 5-74: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 9.05 (s, 1H); 8.52 (q, 1H); 7.77 (d, 1H); 7.72 (d, 1H); 6.88 (t, 1H); 2.81 (d, 1H); 2.37 (s, 3H);

Ex. no. 5-75: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.35 (br s, 1H); 9.05 (s, 1H); 8.60 (t, 1H); 7.77 (d, 1H); 7.72 (d, 1H); 6.88 (t, 1H); 3.32 (m, 2H); 2.39 (s, 3H); 1.14 (t, 3H);

Ex. no. 5-117: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.62 (br s, 1H); 9.07 (s, 1H); 8.74 (t, 1H); 7.89 (s, 2H); 3.31 (m, 2H); 1.11 (t, 3H);

Ex. no. 5-122: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.55 (br s, 1H); 9.07 (s, 1H); 8.70 (q, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 6.95 (t, 1H); 2.80 (d, 3H);

Ex. no. 5-123: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.56 (br s, 1H); 9.06 (s, 1H); 8.77 (t, 1H); 7.82 (d, 1H); 7.74 (d, 1H); 3.29 (m, 2H); 1.13 (t, 3H);

Ex. no. 5-253: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.61 (br s, 1H); 9.07 (s, 1H); 8.19 (s, 1H); 7.96 (s, 1H); 7.89 (d, 1H); 7.86 (d, 1H);

Ex. no. 5-254: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.67 (br s, 1H); 9.59 (t, 1H); 9.08 (s, 1H); 7.96 (s, 2H); 4.41 (d, 2H);

Ex. no. 5-255: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.71 (br s, 1H); 10.85 (br s, 1H); 9.08 (s, 1H); 7.98 (m, 2H); 7.65 (m, 2H); 7.38 (m, 2H); 7.15 (m, 1H);

Ex. no. 6-26: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.18 (br s, 1H); 8.58 (t, 1H); 7.71 (s, 2H); 3.29 (m, 2H); 2.50 (s, 3H); 2.31 (s, 3H); 1.10 (t, 3H);

Ex. no. 6-32: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.11 (br s, 1H); 8.64 (t, 1H); 7.67 (d, 1H); 7.59 (d, 1); 6.89 (t, 1H); 3.30 (m, 2H); 2.49 (s, 3H); 2.31 (s, 3H); 1.12 (t, 3H);

Ex. no. 6-33: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.10 (br s, 1H); 8.70 (d, 1H); 7.67 (d, 1H); 7.58 (d, 1H); 6.89 (t, 1H); 2.85 (m, 1H); 2.49 (s, 3H); 2.28 (s, 3H); 0.70 (m, 2H); 0.53 (m, 2H);

Ex. no. 6-34: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.11 (br s, 1H); 8.78 (t, 1H); 7.68 (d, 1H); 7.60 (d, 1H); 6.90 (t, 1H); 3.15 (m, 2H); 2.49 (s, 3H); 2.33 (s, 3H); 1.04 (m, 1H); 0.46 (m, 2H); 0.23 (m, 2H);

Ex. no. 6-43: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.19 (br s, 1H); 8.49 (q, 1H); 7.77 (d, 1H); 7.61 (d, 1H); 3.80 (s, 3H); 2.77 (d, 3H); 2.49 (s, 3H);

Ex. no. 6-44: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.17 (br s, 1H); 8.57 (t, 1H); 7.76 (d, 1H); 7.62 (d, 1H); 3.81 (s, 3H); 3.27 (m, 2H); 2.49 (s, 3H); 1.10 (t, 3H);

Ex. no. 6-45: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.17 (br s, 1H); 8.64 (d, 1H); 7.76 (d, 1H); 7.61 (d, 1H); 3.80 (s, 3H); 2.79 (m, 1H); 2.49 (s, 3H); 0.70 (m, 2H); 0.47 (m, 2H);

Ex. no. 6-49: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.53 (q, 1H); 7.72 (d, 1H); 7.49 (d, 1H); 6.93 (t, 1H); 3.79 (s, 3H); 2.79 (d, 3H); 2.49 (s, 3H);

Ex. no. 6-50: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.02 (br s, 1H); 8.61 (t, 1H); 7.72 (d, 1H); 7.49 (d, 1H); 6.94 (t, 1H); 3.81 (s, 3H); 3.29 (m, 2H); 2.49 (s, 3H); 1.12 (t, 3H);

Ex. no. 6-51: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.02 (br s, 1H); 8.68 (d, 1H); 7.72 (d, 1H); 7.48 (d, 1H); 6.92 (t, 1H); 3.79 (s, 3H); 2.84 (m, 1H); 2.49 (s, 3H); 0.70 (m, 2H); 0.53 (m, 2H);

Ex. no. 6-58: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.24 (br s, 1H); 8.46 (q, 1H); 7.90 (d, 1H); 7.76 (d, 1H); 2.79 (d, 3H); 2.49 (s, 3H); 2.39 (s, 3H);

Ex. no. 6-60: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.25 br s, 1H); 8.61 (d, 1H); 7.89 (d, 1H); 7.76 (d, 1H); 2.79 (m, 1H); 2.49 (s, 3H); 2.39 (s, 3H); 0.71 (m, 2H); 0.52 (br s, 1H);

Ex. no. 6-74: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.18 (br s, 1H); 8.52 (q, 1H); 7.76 (d, 1H); 7.70 (d, 1H); 6.88 (t, 1H); 2.81 (d, 3H); 2.49 (s, 3H); 2.38 (s, 3H);

Ex. no. 6-75: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.16 (br s, 1H); 8.59 (t, 1H); 7.77 (d, 1H); 7.69 (d, 1H); 6.88 (t, 1H); 3.31 (m, 2H); 2.49 (s, 3H); 2.39 (s, 3H); 1.14 (t, 3H);

Ex. no. 6-76: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.17 (br s, 1H); 8.67 (d, 1H); 7.76 (d, 1H); 7.69 (d, 1H); 6.88 (t, 1H); 2.84 (m, 1H); 2.49 (s, 3H); 2.37 (s, 3H); 0.71 (m, 2H); 0.57 (m, 2H);

Ex. no. 6-116: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.44 (br s, 1H); 8.67 (q, 1H); 7.89 (d, 1H); 7.86 (d, 1H); 2.78 (d, 3H); 2.50 (s, 3H);

Ex. no. 6-117: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.44 (br s, 1H); 8.74 (t, 1H); 7.89 (d, 1H); 7.86 (d, 1H); 3.27 (m, 2H); 2.49 (s, 3H); 1.11 (t, 3H);

Ex. no. 6-118: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.44 (br s, 1H); 8.81 (d, 1H); 7.88 (d, 1H); 7.85 (d, 1H); 2.79 (m, 1H); 2.49 (s, 3H); 0.72 (m, 2H); 0.50 (br s, 2H);

Ex. no. 6-120: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.51 (br s, 1H); 9.54 (t, 1H); 7.93 (s, 2H); 4.14 (m, 2H); 2.52 (s, 3H);

Ex. no. 6-124: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.36 (br s, 1H); 8.83 (d, 1H); 7.80 (d, 1H); 7.72 (d, 1H); 6.93 (t, 1H); 2.83 (m, 1H); 2.48 (s, 3H); 0.71 (m, 2H); 0.54 (m, 2H);

Ex. no. 6-141: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.31 (br s, 1H); 8.69 (t, 1H); 7.76 (d, 1H); 7.57 (d, 1H); 3.27 (m, 2H); 2.48 (s, 3H); 1.13 (t, 3H);

Ex. no. 6-143: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.31 (br s, 1H); 8.79 (t, 1H); 7.76 (d, 1H); 7.57 (d, 1H); 3.15 (m, 2H); 2.49 (s, 3H); 1.01 (m, 1H); 0.44 (m, 2H); 0.25 (m, 2H);

Ex. no. 6-144: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.32 (br s, 1H); 9.48 (t, 1H); 7.80 (d, 1H); 7.63 (d, 1H); 4.12 (m, 2H); 2.49 (s, 3H);

Ex. no. 6-145: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.31 (br s, 1H); 9.21 (t, 1H); 7.78 (d, 1H); 7.61 (d, 1H); 6.13 (tt, 1H); 3.69 (m, 2H); 2.49 (s, 3H);

Ex. no. 6-159: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.41 (br s, 1H); 8.72 (t, 1H); 7.92 (d, 1H); 7.80 (d, 1H); 3.28 (m, 2H); 2.50 (s, 3H); 1.11 (t, 3H);

Ex. no. 6-161: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.42 (br s, 1H); 8.82 (t, 1H); 7.91 (d, 1H); 7.80 (d, 1H); 3.13 (m, 2H); 2.49 (s, 3H); 1.00 (m, 1H); 0.45 (m, 2H); 0.23 (m, 2H);

Ex. no. 6-165: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.35 (br s, 1H); 8.75 (t, 1H); 7.77 (d, 1H); 7.74 (d, 1H); 6.91 (t, 1H); 3.29 (m, 2H); 2.49 (s, 3H); 1.13 (t, 3H);

Ex. no. 6-166: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.36 (br s, 1H); 8.81 (d, 1H); 7.76 (d, 1H); 7.73 (d, 1H); 6.91 (t, 1H); 2.80 (m, 1H); 2.49 (s, 3H); 0.71 (m, 2H); 0.56 (m, 2H);

Ex. no. 6-167: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.35 (br s, 1H); 8.88 (t, 1H); 7.78 (d, 1H); 7.74 (d, 1H); 6.91 (t, 1H); 3.15 (m, 2H); 2.49 (s, 3H); 1.03 (m, 1H); 0.46 (m, 2H); 0.24 (m, 2H);

Ex. no. 6-168: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 9.52 (t, 1H); 7.80 (s, 2H); 6.90 (t, 1H); 4.13 (m, 2H); 2.49 (s, 3H);

Ex. no. 6-169: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.37 (br s, 1H) M 9.26 (t, 1H); 7.80 (d, 1H); 7.78 (d, 1H); 6.92 (t, 1H); 6.17 (tt, 1H); 3.71 (m, 2H); 2.49 (s, 3H);

Ex. no. 6-210: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.22 (br s, 1H); 8.52 (q, 1H); 7.72 (s, 2H); 2.78 (d, 3H); 2.66 (m, 2H); 2.46 (s, 3H); 1.13 (t, 3H);

Ex. no. 6-211: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.21 (br s, 1H); 8.61 (t, 1H); 7.72 (br s, 2H); 3.28 (m, 2H); 2.78 (m, 1H); 2.69 (m, 1H); 2.49 (s, 3H); 1.15 (t, 3H); 1.10 (t, 3H);

Ex. no. 6-212: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.19 (br s, 1H); 8.66 (d, 1H); 7.71 (s, 2H); 2.80 (m, 2H); 2.68 (m, 1H); 2.52 (s, 3H); 1.13 (t, 3H); 0.71 (m, 2H); 0.48 (m, 2H);

Ex. no. 6-228: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.08 (br s, 1H); 8.61 (t, 1H); 7.73 (d, 1H); 7.63 (d, 1H); 3.12 (m, 2H); 2.49 (s, 3H); 2.11 (m, 1H); 1.02 (m, 1H); 0.80 (m, 2H); 0.62 (m, 2H); 0.46 (m, 2H); 0.22 (m, 2H);

Ex. no. 6-230: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.11 (br s, 1H); 9.01 (t, 1H); 7.76 (d, 1H); 7.67 (d, 1H); 6.12 (tt, 1H); 3.68 (m, 2H); 2.49 (s, 3H); 2.10 (m, 1H); 0.83 (m, 2H); 0.59 (m, 2H);

Ex. no. 6-231: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.51 (q, 1H); 7.63 (d, 1H); 7.60 (d, 1H); 6.92 (t, 1H); 2.81 (d, 3H); 2.49 (s, 3H); 2.13 (m, 1H); 0.79 (m, 2H); 0.51 (m, 2H);

Ex. no. 6-233: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.01 (br s, 1H); 8.66 (d, 1H); 7.60 (m, 2H); 6.92 (t, 1H); 2.84 (m, 1H); 2.49 (s, 3H); 2.12 (m, 1H); 0.79 (m, 2H); 0.70 (m, 2H); 0.54 (m, 4H);

Ex. no. 6-252: ¹H-NMR (400 MHz, DMSO-d₆): δ=11.82 (br s, 1H); 7.91 (br s, 2H); 4.30 (br s, 1H); 2.38 (s, 3H); 1.99 (s, 3H);

Ex. no. 6-253: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.45 (br s, 1H); 8.20 (s, 1H); 7.98 (s, 1H); 7.89 (d, 1H); 7.86 (d, 1H); 2.52 (s, 3H);

Ex. no. 6-254: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.44 (br s, 1H); 8.73 (d, 1H); 7.85 (d, 1H); 7.88 (d, 1H); 3.43 (m, 1H); 1.19 (m, 3H); 0.89 (m, 1H); 0.42 (m, 2H); 0.29 (m, 2H);

Ex. no. 6-255: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.19 (br s, 1H); 8.50 (d, 1H); 7.70 (s, 2H); 4.07 (m, 1H); 2.49 (s, 3H); 2.31 (s, 3H); 1.15 (d, 3H); 1.11 (d, 3H);

Ex. no. 6-256: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.20 (br s, 1H); 8.84 (d, 1H); 7.71 (s, 2H); 4.36 (m, 1H); 2.49 (s, 3H); 2.30 (s, 3H); 2.24 (m, 2H); 1.97 (m, 2H); 1.48 (m, 2H);

Ex. no. 6-257: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.31 (br s, 1H); 8.65 (d, 1H); 7.75 (d, 1H); 7.57 (d, 1H); 3.48 (m, 1H); 2.49 (s, 3H); 1.21 (d, 3H); 0.91 (m, 1H); 0.42 (m, 2H); 0.34 (m, 2H);

Ex. no. 6-258: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.11 (br s, 1H); 8.69 (d, 1H); 7.68 (d, 1H); 7.59 (d, 1H); 6.89 (t, 1H); 3.44 (m, 1H); 2.49 (s, 3H); 2.34 (s, 3H); 1.22 (d, 3H); 0.92 (m, 1H); 0.43 (m, 2H); 0.34 (m, 1H); 0.26 (m, 1H);

Ex. no. 6-259: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 8.79 (t, 1H); 7.80 (d, 1H); 7.74 (d, 1H); 6.92 (t, 1H); 3.23 (m, 2H); 2.49 (s, 3H); 1.54 (m, 2H); 0.92 (t, 3H);

Ex. no. 6-260: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 8.69 (d, 1H); 7.79 (d, 1H); 7.73 (d, 1H); 6.92 (t, 1H); 4.08 (m, 1H); 2.49 (s, 3H); 1.16 (d, 6H);

Ex. no. 6-261: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 9.03 (d, 1H); 7.80 (d, 1H); 7.73 (d, 1H); 6.91 (t, 1H); 4.36 (m, 1H); 2.49 (s, 3H); 2.26 (m, 2H); 2.01 (m, 2H); 1.69 (m, 2H);

Ex. no. 6-262: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 8.90 (t, 1H); 7.80 (d, 1H); 7.74 (d, 1H); 6.94 (t, 1H); 3.45 (m, 4H); 3.28 (s, 3H); 2.49 (s, 3H);

Ex. no. 6-263: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.35 (br s, 1H); 8.91 (t, 1H); 7.80 (d, 1H); 7.73 (d, 1H); 6.95 (t, 1H); 3.98 (m, 1H); 3.78 (m, 1H); 3.65 (m, 1H); 3.34 (m, 2H); 2.49 (s, 3H); 1.94 (m, 1H); 1.84 (m, 2H); 1.62 (m, 1H);

Ex. no. 6-264: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.38 (br s, 1H); 9.43 (t, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 7.45 (m, 1H); 7.07 (m, 1H); 6.99 (m, 1H); 6.90 (t, 1H); 4.67 (d, 3H); 2.49 (s, 3H);

Ex. no. 6-265: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.39 (br s, 1H); 9.10 (t, 1H); 7.83 (d, 1H); 7.79 (d, 1H); 7.57 (t, 1H); 4.16 (d, 2H); 3.01 (s, 3H); 2.88 (s, 3H);

Ex. no. 6-266: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.41 (br s, 1H); 10.83 (br s, 1H); 7.88 (d, 1H); 7.80 (d, 1H); 7.69 (m, 2H); 7.37 (m, 2H); 7.15 (m, 1H); 7.10 (t, 1H); 2.49 (s, 3H);

Ex. no. 6-267: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.35 (br s, 1H); 8.77 (d, 1H); 7.75 (m, 2H); 6.89 (t, 1H); 3.45 (m, 1H); 2.49 (s, 3H); 1.22 (d, 3H); 0.92 (m, 1H); 0.41 (m, 3H); 0.28 (m, 1H);

Ex. no. 6-268: ¹H-NMR (400 MHz, DMSO-d₆): δ=12.08 (br s, 1H); 8.53 (d, 1H); 7.73 (d, 1H); 7.62 (d, 1H); 3.36 (m, 1H); 2.49 (s, 3H); 2.21 (m, 1H); 1.20 (d, 3H); 0.89 (m, 1H); 0.83 (m, 2H); 0.63 (br s, 2H); 0.44 (m, 2H); 0.32 (m, 1H); 0.24 (m, 1H).

B. FORMULATION EXAMPLES

-   -   a) A dusting product is obtained by mixing 10 parts by weight of         a compound of the formula (I) and/or salts thereof and 90 parts         by weight of talc as an inert substance and comminuting the         mixture in a hammer mill.     -   b) A readily water-dispersible, wettable powder is obtained by         mixing 25 parts by weight of a compound of the formula (I)         and/or salts thereof, 64 parts by weight of kaolin-containing         quartz as an inert substance, 10 parts by weight of potassium         lignosulfonate and 1 part by weight of sodium         oleoylmethyltaurate as a wetting agent and dispersant, and         grinding the mixture in a pinned-disk mill.     -   c) A readily water-dispersible dispersion concentrate is         obtained by mixing 20 parts by weight of a compound of the         formula (I) and/or salts thereof with 6 parts by weight of         alkylphenol polyglycol ether (® Triton X 207), 3 parts by weight         of isotridecanol polyglycol ether (8 EO) and 71 parts by weight         of paraffinic mineral oil (boiling range for example about 255         to above 277° C.), and grinding the mixture in a friction ball         mill to a fineness of below 5 microns.     -   d) An emulsifiable concentrate is obtained from 15 parts by         weight of a compound of the formula (I) and/or salts thereof, 75         parts by weight of cyclohexanone as a solvent and 10 parts by         weight of ethoxylated nonylphenol as an emulsifier.     -   e) Water-dispersible granules are obtained by mixing         -   75 parts by weight of a compound of the formula (I) and/or             salts thereof,         -   10 parts by weight of calcium lignosulfonate,         -   5 parts by weight of sodium lauryl sulfate,         -   3 parts by weight of polyvinyl alcohol and         -   7 parts by weight of kaolin,         -   grinding the mixture in a pinned-disk mill, and granulating             the powder in a fluidized bed by spray application of water             as a granulating liquid.     -   f) Water-dispersible granules are also obtained by homogenizing         and precomminuting, in a colloid mill,         -   25 parts by weight of a compound of the formula (I) and/or             salts thereof,         -   5 parts by weight of sodium             2,2′-dinaphthylmethane-6,6′-disulfonate         -   2 parts by weight of sodium oleoylmethyltaurate,         -   1 part by weight of polyvinyl alcohol,         -   17 parts by weight of calcium carbonate and         -   50 parts by weight of water,         -   then grinding the mixture in a bead mill and atomizing and             drying the resulting suspension in a spray tower by means of             a one-phase nozzle.

C. BIOLOGICAL EXAMPLES

The abbreviations used for the harmful plants mean:

ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AVEFA Avena fatua AMARE Amaranthus retroflexus CYPES Cyperus esculentus DIGSA Digitaria sanguinalis ECHCG Echinochloa crus-galli HORMU Hordeum murinum LOLMU Lolium multiflorum LOLRI Lolium rigidum MATIN Matricaria inodora PHBPU Pharbitis purpurea POLCO Polygonum convolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronica persica VIOTR Viola tricolor

1. Pre-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fiber pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at a water application rate equivalent to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Numerous compounds of the invention showed very good action against a multitude of important harmful plants. The tables below illustrate, in an illustrative manner, the post-emergence herbicidal action of the compounds of the invention, the herbicidal activity being stated in percent.

TABLE 1a Pre-emergence action at 20 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 80 2-338 20 90 3-338 20 90 2-337 20 100 3-337 20 100 1-26 20 100 2-26 20 100 3-26 20 100 6-26 20 100 1-208 20 100 2-208 20 100 3-208 20 100 6-159 20 100 1-130 20 100 2-130 20 100 1-131 20 100 2-131 20 100 6-118 20 100 1-149 20 100 2-149 20 100 6-124 20 100 5-59 20 100 5-58 20 90 5-117 20 100 5-253 20 90 5-75 20 100 5-74 20 80 5-123 20 100 5-122 20 90 1-82 20 100 1-87 20 100 2-87 20 100 1-88 20 100 2-88 20 100 1-209 20 100 2-25 20 100 3-27 20 100 1-27 20 100 2-27 20 100 1-173 20 90 2-173 20 90 1-273 20 100 2-273 20 90 3-273 20 90 6-212 20 80 1-44 20 100 2-44 20 100 1-45 20 80 2-45 20 80 1-46 20 90 2-46 20 100 1-30 20 100 1-31 20 100 2-31 20 100 1-28 20 90 2-28 20 100 2-29 20 100 1-304 20 100 2-304 20 100 1-305 20 100 2-305 20 100 1-306 20 100 2-306 20 100 2-177 20 90 1-178 20 90 1-179 20 80 1-132 20 100 2-132 20 100 1-135 20 100 2-135 20 100 6-254 20 100 2-134 20 100 6-120 20 80 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 100 1-279 20 100 2-279 20 80 2-195 20 100 2-225 20 100 1-197 20 100 2-227 20 100 1-227 20 100 2-226 20 80 2-196 20 100 2-57 20 100 2-58 20 100 2-56 20 100 1-57 20 100 1-207 20 100 2-207 20 100 2-271 20 100 2-32 20 100 1-34 20 80 2-34 20 80 6-255 20 100 2-33 20 100 2-42 20 100 1-146 20 100 1-72 20 100 2-72 20 100 1-73 20 100 2-73 20 100 1-74 20 100 2-74 20 100 1-138 20 100 2-138 20 80 1-137 20 100 1-136 20 90 1-180 20 90 2-180 20 100 6-143 20 100 1-183 20 100 2-183 20 100 1-182 20 100 2-182 20 100 6-145 20 100 1-181 20 90 2-181 20 100 2-36 20 90 1-228 20 100 2-228 20 100 6-167 20 90 1-230 20 90 2-230 20 100 2-286 20 100 1-287 20 100 2-287 20 100 2-288 20 100 1-210 20 100 2-210 20 100 1-212 20 80 2-213 20 100 1-288 20 100 1-289 20 100 2-289 20 100 1-291 20 100 2-291 20 100 2-292 20 100 1-271 20 100 2-47 20 100 1-339 20 90 2-339 20 100 6-258 20 100 1-49 20 80 2-49 20 100 1-229 20 90 2-229 20 80 1-340 20 100 6-267 20 90 2-340 20 100 1-47 20 100 1-33 20 90 1-32 20 100 2-154 20 100 6-259 20 90 1-155 20 100 2-155 20 100 6-260 20 90 1-164 20 80 2-164 20 90 6-261 20 80 1-165 20 90 1-166 20 90 2-156 20 100 1-159 20 80 2-161 20 90 2-211 20 100 2-272 20 100 1-161 20 80 2-276 20 100 1-276 20 100 1-211 20 100 1-274 20 100 1-272 20 90 6-211 20 90 1-341 20 100 1-292 20 100 2-341 20 100 1-83 20 100 2-83 20 100 1-89 20 90 2-89 20 100 6-161 20 100 6-268 20 100 2-342 20 100 1-344 20 90 1-345 20 100 2-344 20 100 1-346 20 90 2-345 20 90 2-346 20 80 1-195 20 90 2-184 20 100 1-185 20 100 2-185 20 100 1-186 20 100 2-186 20 100 1-84 20 100 2-84 20 100 1-352 20 100 2-350 20 100 1-86 20 100 2-86 20 100 1-92 20 100 2-92 20 100 1-90 20 100 2-90 20 100 1-353 20 100 2-351 20 80 2-354 20 90

TABLE 1b Pre-emergence action at 80 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 100 6-253 80 90 1-337 80 100 2-337 80 100 3-337 80 100 6-252 80 80 1-123 80 100 2-123 80 100 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 100 2-125 80 100 3-125 80 100 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 100 2-81 80 100 2-82 80 100 6-58 80 100 1-147 80 90 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 100 6-124 80 100 5-59 80 100 5-58 80 100 5-117 80 100 5-253 80 100 5-75 80 100 5-74 80 100 5-123 80 100 5-122 80 100 1-82 80 100 1-87 80 100 2-87 80 100 1-88 80 100 2-88 80 100 1-209 80 100 1-4 80 100 1-25 80 100 2-25 80 100 3-27 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 90 3-273 80 100 6-212 80 90 4-212 80 90 1-44 80 100 2-44 80 100 1-45 80 100 2-45 80 100 6-32 80 80 1-46 80 100 2-46 80 100 6-33 80 90 1-30 80 100 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 100 2-29 80 100 1-304 80 100 2-304 80 100 1-305 80 100 2-305 80 100 1-306 80 100 2-306 80 100 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 100 1-134 80 90 2-134 80 100 1-133 80 100 2-133 80 100 6-120 80 100 1-277 80 100 2-277 80 100 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 100 1-225 80 80 1-226 80 90 2-226 80 80 6-165 80 100 6-166 80 100 2-196 80 100 1-56 80 90 6-45 80 90 2-57 80 100 6-43 80 100 1-58 80 80 2-58 80 100 2-56 80 100 1-57 80 100 1-207 80 100 2-207 80 100 2-271 80 100 6-210 80 100 2-32 80 100 1-34 80 100 2-34 80 100 6-255 80 100 2-33 80 100 2-42 80 100 6-256 80 100 2-146 80 90 1-143 80 100 5-255 80 100 5-254 80 100 1-146 80 100 2-143 80 100 1-72 80 100 2-72 80 100 1-73 80 100 2-73 80 100 6-50 80 90 1-74 80 100 2-74 80 100 6-51 80 100 1-138 80 100 2-138 80 100 1-137 80 100 1-136 80 100 1-180 80 100 2-180 80 100 6-143 80 100 1-183 80 100 2-183 80 100 6-257 80 100 1-182 80 100 2-182 80 100 6-145 80 100 1-181 80 100 2-181 80 100 6-144 80 90 1-36 80 100 2-36 80 100 1-228 80 100 2-228 80 100 6-167 80 100 1-230 80 100 2-230 80 100 6-169 80 90 2-286 80 100 1-287 80 100 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 100 2-213 80 100 1-288 80 100 1-289 80 100 2-289 80 100 6-228 80 90 1-291 80 100 2-291 80 100 6-230 80 90 2-292 80 100 1-271 80 100 2-47 80 100 6-34 80 100 1-339 80 100 2-339 80 100 6-258 80 100 1-49 80 100 2-49 80 100 1-41 80 100 1-229 80 100 2-229 80 100 1-340 80 100 6-267 80 100 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 100 1-155 80 100 2-155 80 100 6-260 80 100 1-164 80 80 2-164 80 100 6-261 80 100 1-165 80 100 1-166 80 100 1-156 80 100 2-156 80 100 6-262 80 100 1-159 80 100 2-159 80 100 1-160 80 80 2-160 80 90 2-161 80 100 6-266 80 80 2-211 80 100 2-272 80 100 1-161 80 90 2-276 80 100 1-276 80 100 1-211 80 100 1-274 80 100 6-168 80 100 1-272 80 100 6-211 80 100 1-341 80 100 1-292 80 100 2-341 80 100 2-158 80 100 1-83 80 100 2-83 80 100 6-60 80 90 1-89 80 100 2-89 80 100 6-161 80 100 6-268 80 100 1-343 80 100 2-342 80 100 1-344 80 100 2-343 80 100 1-345 80 100 2-344 80 100 1-346 80 100 2-345 80 100 1-347 80 100 2-346 80 90 2-347 80 100 1-195 80 100 1-184 80 100 2-184 80 100 1-185 80 100 2-185 80 100 1-186 80 100 2-186 80 100 1-350 80 100 2-348 80 100 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 100 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 100 1-92 80 100 2-92 80 100 1-90 80 100 2-90 80 100 1-353 80 100 2-351 80 100 1-354 80 100 2-352 80 100 1-355 80 100 2-353 80 100 1-356 80 100 2-354 80 100

TABLE 1c Pre-emergence action at 3200 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 100 6-252 320 90 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 2a Pre-emergence action at 20 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 2-129 20 90 1-129 20 90 1-208 20 80 2-208 20 80 1-130 20 100 2-130 20 90 1-131 20 80 2-131 20 90 1-149 20 80 2-149 20 80 1-173 20 80 2-173 20 100 1-177 20 80 2-177 20 90 1-178 20 80 2-178 20 80 1-179 20 80 2-179 20 80 1-132 20 80 1-134 20 80 1-133 20 90 6-120 20 80 2-278 20 80 2-279 20 80 1-197 20 100 2-227 20 80 1-227 20 80 2-196 20 90 2-58 20 90 2-207 20 80 2-32 20 90 1-34 20 80 2-34 20 80 6-255 20 90 2-33 20 90 2-42 20 80 6-256 20 80 1-137 20 90 2-180 20 80 1-182 20 80 2-287 20 80 1-212 20 100 1-32 20 80 2-155 20 80 1-166 20 90 2-276 20 90 1-276 20 90 1-211 20 90 1-274 20 80 1-272 20 90 1-341 20 80 1-292 20 80 2-341 20 80 1-83 20 80 2-83 20 90 1-342 20 90 2-342 20 90 1-344 20 90 2-343 20 80 1-345 20 80 2-344 20 80 1-195 20 90 1-184 20 90 2-184 20 90 1-185 20 90 2-348 20 90 1-351 20 100

TABLE 2b Pre-emergence action at 80 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 3-129 80 80 2-129 80 100 1-129 80 100 6-116 80 100 2-338 80 90 3-338 80 80 2-337 80 90 3-337 80 100 1-26 80 100 2-26 80 100 3-26 80 80 6-26 80 80 1-208 80 100 2-208 80 90 3-208 80 90 6-159 80 80 1-130 80 100 2-130 80 100 1-81 80 80 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 90 2-149 80 90 6-124 80 90 5-117 80 90 5-123 80 80 5-122 80 80 1-82 80 80 1-87 80 90 2-87 80 80 1-88 80 90 2-88 80 90 1-209 80 80 1-4 80 80 1-25 80 90 2-25 80 90 3-27 80 90 1-27 80 90 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 90 2-273 80 90 6-212 80 80 1-44 80 90 2-44 80 80 1-45 80 90 2-45 80 90 1-46 80 90 2-46 80 100 1-30 80 80 2-30 80 100 1-31 80 90 2-31 80 80 1-28 80 90 2-28 80 90 1-29 80 100 2-29 80 80 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 6-141 80 90 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 90 1-135 80 90 2-135 80 90 6-254 80 90 1-134 80 100 2-134 80 90 1-133 80 90 2-133 80 90 6-120 80 90 1-277 80 90 1-278 80 90 2-278 80 90 1-279 80 80 2-279 80 90 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 90 1-225 80 100 1-226 80 90 2-226 80 90 6-165 80 80 2-196 80 100 1-56 80 90 2-57 80 90 1-58 80 90 2-58 80 100 2-56 80 90 1-57 80 80 1-207 80 100 2-207 80 90 2-271 80 80 2-32 80 100 1-34 80 100 2-34 80 90 6-255 80 100 2-33 80 100 2-42 80 90 6-256 80 90 2-146 80 80 1-146 80 90 1-141 80 90 1-37 80 100 2-37 80 90 2-72 80 80 1-73 80 80 2-73 80 100 1-74 80 90 2-74 80 100 1-138 80 90 2-138 80 90 2-141 80 90 1-137 80 90 1-136 80 90 1-180 80 100 2-180 80 100 1-183 80 90 2-183 80 90 1-182 80 100 2-182 80 80 6-145 80 90 1-181 80 100 2-181 80 80 1-228 80 90 2-228 80 80 1-230 80 90 2-286 80 80 2-287 80 90 2-288 80 90 1-210 80 80 2-210 80 100 1-212 80 100 2-212 80 100 1-288 80 90 1-289 80 90 2-289 80 90 1-291 80 80 2-291 80 80 2-292 80 90 1-271 80 90 2-47 80 100 6-34 80 80 1-339 80 90 2-339 80 90 6-258 80 90 1-49 80 80 2-49 80 90 1-229 80 90 2-229 80 90 1-340 80 90 6-267 80 80 1-47 80 90 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 80 1-155 80 90 2-155 80 100 6-260 80 90 1-164 80 100 1-165 80 100 1-166 80 100 1-156 80 90 2-156 80 100 2-159 80 80 1-162 80 90 2-211 80 90 2-272 80 90 2-276 80 90 1-276 80 100 1-211 80 100 1-274 80 90 6-168 80 80 1-272 80 100 6-211 80 90 1-341 80 90 1-292 80 90 2-341 80 90 1-83 80 100 2-83 80 90 1-89 80 90 2-89 80 100 6-161 80 90 1-342 80 100 1-343 80 100 2-342 80 100 1-344 80 100 2-343 80 90 1-345 80 90 2-344 80 100 1-346 80 90 2-345 80 80 1-347 80 80 2-346 80 80 1-195 80 90 1-184 80 100 2-184 80 100 1-185 80 100 2-185 80 90 1-186 80 90 2-186 80 100 1-349 80 100 1-350 80 100 2-348 80 100 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 90 1-352 80 80 1-86 80 100 2-86 80 90 1-92 80 90 2-92 80 90 1-90 80 80 1-353 80 90 2-351 80 80 1-354 80 80 2-352 80 90 1-355 80 90 2-353 80 90 1-356 80 100 2-354 80 90

TABLE 2c Pre-emergence action at 320 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 90 2-337 320 100 6-117 320 90 1-81 320 100 2-81 320 90 2-82 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 3a Pre-emergence action at 20 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 100 2-338 20 90 3-338 20 80 1-337 20 90 2-337 20 90 3-337 20 100 6-252 20 80 1-123 20 80 2-123 20 80 1-26 20 100 2-26 20 100 3-26 20 100 6-26 20 100 1-208 20 100 2-208 20 100 3-208 20 100 6-159 20 100 1-125 20 90 2-125 20 80 1-130 20 100 2-130 20 100 1-131 20 100 2-131 20 100 6-118 20 80 1-149 20 100 2-149 20 100 6-124 20 100 5-59 20 100 5-58 20 100 5-117 20 90 5-253 20 100 5-75 20 100 5-74 20 100 5-123 20 100 5-122 20 80 1-82 20 90 1-87 20 90 2-87 20 100 1-88 20 100 2-88 20 100 1-209 20 100 1-4 20 90 1-25 20 100 2-25 20 100 3-27 20 100 1-27 20 100 2-27 20 100 1-173 20 100 2-173 20 100 1-273 20 100 2-273 20 90 3-273 20 100 6-212 20 90 4-212 20 90 1-44 20 100 2-44 20 100 1-45 20 100 2-45 20 100 6-32 20 80 1-46 20 100 2-46 20 100 6-33 20 90 1-30 20 100 2-30 20 100 1-31 20 100 2-31 20 100 1-28 20 100 2-28 20 100 1-29 20 100 2-29 20 100 1-304 20 100 2-304 20 100 1-305 20 100 2-305 20 100 1-306 20 100 2-306 20 90 1-177 20 100 2-177 20 100 1-178 20 100 2-178 20 100 1-179 20 100 2-179 20 100 1-132 20 100 2-132 20 100 1-135 20 100 2-135 20 100 6-254 20 100 1-134 20 100 2-134 20 100 1-133 20 90 2-133 20 90 6-120 20 100 1-277 20 100 2-277 20 100 1-278 20 100 2-278 20 100 1-279 20 100 2-279 20 100 2-195 20 100 2-225 20 100 1-197 20 100 2-227 20 100 1-227 20 100 2-197 20 100 1-225 20 100 1-226 20 100 2-226 20 100 6-165 20 100 6-166 20 90 2-196 20 100 1-56 20 100 6-45 20 80 6-44 20 80 2-57 20 100 1-58 20 100 2-58 20 100 2-56 20 100 1-57 20 100 1-207 20 100 2-207 20 100 2-271 20 100 2-32 20 100 1-34 20 100 2-34 20 90 6-255 20 100 2-33 20 100 2-42 20 100 6-256 20 90 2-146 20 100 5-255 20 90 1-146 20 100 1-141 20 100 1-37 20 100 2-37 20 90 1-72 20 100 2-72 20 100 6-49 20 80 1-73 20 100 2-73 20 100 6-50 20 100 1-74 20 100 2-74 20 100 6-51 20 80 1-144 20 90 2-144 20 80 1-138 20 100 2-138 20 100 2-141 20 100 1-137 20 100 1-136 20 100 1-180 20 100 2-180 20 100 6-143 20 100 1-183 20 100 2-183 20 90 1-182 20 100 2-182 20 100 6-145 20 90 1-181 20 100 2-181 20 100 6-144 20 90 1-36 20 100 2-36 20 100 1-228 20 100 2-228 20 100 6-167 20 100 1-230 20 100 2-230 20 100 6-169 20 90 2-286 20 100 1-287 20 100 2-287 20 100 2-288 20 100 1-210 20 100 2-210 20 100 1-212 20 100 2-213 20 100 1-288 20 100 1-289 20 90 2-289 20 100 1-291 20 100 2-291 20 100 6-230 20 100 2-292 20 100 1-271 20 100 2-47 20 100 6-34 20 100 1-339 20 100 2-339 20 100 6-258 20 100 1-49 20 100 2-49 20 100 1-41 20 90 1-229 20 100 2-229 20 100 1-340 20 100 6-267 20 90 2-340 20 100 1-47 20 100 1-33 20 100 1-32 20 100 2-154 20 100 6-259 20 100 1-155 20 100 2-155 20 100 6-260 20 100 2-164 20 100 6-261 20 100 1-165 20 100 1-166 20 100 1-156 20 100 2-156 20 100 6-262 20 90 1-159 20 100 2-159 20 100 1-162 20 90 2-162 20 90 6-264 20 80 1-160 20 100 2-160 20 100 2-161 20 90 6-266 20 90 2-211 20 100 2-272 20 100 1-161 20 100 2-276 20 100 1-276 20 90 1-211 20 100 1-274 20 100 6-168 20 90 1-272 20 100 6-211 20 100 1-341 20 100 1-292 20 100 2-341 20 100 1-158 20 100 2-83 20 100 1-89 20 100 2-89 20 90 6-161 20 100 1-342 20 100 1-343 20 100 2-342 20 90 1-344 20 100 2-343 20 100 1-345 20 100 2-344 20 100 1-346 20 100 2-345 20 100 2-346 20 100 1-195 20 90 1-184 20 100 2-184 20 100 1-185 20 100 2-185 20 100 1-186 20 80 2-186 20 100 1-349 20 100 1-350 20 100 2-348 20 100 1-351 20 100 2-349 20 100 1-84 20 100 2-84 20 100 1-352 20 100 2-350 20 100 1-86 20 100 2-86 20 100 1-92 20 100 2-92 20 100 1-90 20 100 2-90 20 100 1-353 20 100 2-351 20 100 2-352 20 100 1-355 20 100 2-353 20 100 1-356 20 100 2-354 20 100

TABLE 3b Pre-emergence action at 80 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 100 6-253 80 80 1-337 80 100 2-337 80 100 3-337 80 100 6-252 80 90 1-123 80 100 2-123 80 100 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 100 1-125 80 100 2-125 80 100 3-125 80 100 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 100 2-81 80 100 2-82 80 100 6-58 80 100 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 100 6-124 80 100 5-59 80 100 5-58 80 100 5-117 80 90 5-253 80 100 5-75 80 100 5-74 80 100 5-123 80 100 5-122 80 100 1-82 80 100 1-87 80 100 2-87 80 100 1-88 80 100 2-88 80 100 1-209 80 100 1-4 80 100 1-25 80 100 2-25 80 100 3-27 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 100 3-273 80 100 6-212 80 90 4-212 80 90 1-44 80 100 2-44 80 100 1-45 80 100 2-45 80 100 6-32 80 100 1-46 80 100 2-46 80 100 6-33 80 100 1-30 80 100 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 100 2-29 80 100 1-304 80 100 2-304 80 100 6-231 80 100 1-305 80 100 2-305 80 100 1-306 80 100 2-306 80 100 6-233 80 80 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 6-141 80 100 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 100 1-134 80 100 2-134 80 100 1-133 80 100 2-133 80 100 6-120 80 100 1-277 80 100 2-277 80 100 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 100 1-225 80 100 1-226 80 100 2-226 80 100 6-165 80 100 6-166 80 100 2-196 80 100 1-56 80 100 6-45 80 100 6-44 80 100 2-57 80 100 6-43 80 100 1-58 80 100 2-58 80 100 2-56 80 100 1-57 80 100 1-207 80 100 2-207 80 100 2-271 80 100 6-210 80 100 2-32 80 100 1-34 80 100 2-34 80 100 6-255 80 100 2-33 80 100 2-42 80 100 6-256 80 100 2-146 80 100 2-142 80 100 1-143 80 100 5-255 80 100 1-142 80 100 5-254 80 100 1-140 80 100 1-146 80 100 1-141 80 100 1-37 80 100 2-37 80 100 2-143 80 100 1-72 80 100 2-72 80 100 6-49 80 100 1-73 80 100 2-73 80 100 6-50 80 100 1-74 80 100 2-74 80 100 6-51 80 100 2-35 80 90 1-144 80 100 2-144 80 100 1-138 80 100 2-138 80 100 2-141 80 100 1-137 80 100 1-136 80 100 1-180 80 100 2-180 80 100 6-143 80 100 1-183 80 100 2-183 80 100 6-257 80 100 1-182 80 100 2-182 80 100 6-145 80 100 1-181 80 100 2-181 80 100 6-144 80 100 1-36 80 100 2-36 80 100 1-228 80 100 2-228 80 100 6-167 80 100 1-230 80 100 2-230 80 100 6-169 80 100 2-286 80 100 1-287 80 100 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 100 2-213 80 100 1-288 80 100 1-289 80 100 2-289 80 100 6-228 80 100 1-291 80 100 2-291 80 100 6-230 80 100 2-292 80 100 1-271 80 100 2-47 80 100 6-34 80 100 1-339 80 100 2-339 80 100 6-258 80 100 1-49 80 100 2-49 80 100 1-41 80 100 1-229 80 100 2-229 80 100 1-340 80 100 6-267 80 100 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 100 1-155 80 100 2-155 80 100 6-260 80 100 1-164 80 100 2-164 80 100 6-261 80 100 1-165 80 100 1-166 80 100 1-156 80 100 2-156 80 100 6-262 80 100 1-157 80 100 2-157 80 90 1-159 80 100 2-159 80 100 1-162 80 100 2-162 80 100 6-264 80 100 1-160 80 100 2-160 80 100 6-265 80 80 2-161 80 100 6-266 80 100 2-211 80 100 2-272 80 100 1-161 80 100 2-276 80 100 1-276 80 100 1-211 80 100 1-274 80 100 6-168 80 100 1-272 80 100 6-211 80 100 1-341 80 100 1-292 80 100 2-341 80 100 1-158 80 100 2-158 80 100 1-83 80 100 2-83 80 100 6-60 80 100 1-89 80 100 2-89 80 100 6-76 80 100 6-161 80 100 6-268 80 100 1-342 80 100 1-343 80 100 2-342 80 100 1-344 80 100 2-343 80 100 1-345 80 100 2-344 80 100 1-346 80 100 2-345 80 100 1-347 80 100 2-346 80 100 1-195 80 100 1-184 80 100 2-184 80 100 1-185 80 100 2-185 80 100 1-186 80 100 2-186 80 100 1-349 80 100 1-350 80 100 2-348 80 100 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 100 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 100 1-92 80 100 2-92 80 100 1-90 80 100 2-90 80 100 1-353 80 100 2-351 80 100 1-354 80 100 2-352 80 100 1-355 80 100 2-353 80 100 1-356 80 100 2-354 80 100

TABLE 3c Pre-emergence action at 320 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 90 2-337 320 100 6-252 320 90 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 4a Pre-emergence action at 20 g/ha against AVEFA in % Example number Dosage [g/ha] AVEFA 2-129 20 100 1-129 20 100 2-337 20 90 2-26 20 80 3-26 20 80 1-208 20 80 1-130 20 100 2-130 20 90 1-131 20 80 1-149 20 80 2-149 20 80 2-27 20 80 2-173 20 90 1-29 20 80 1-177 20 80 2-178 20 90 1-135 20 80 1-134 20 80 2-134 20 80 2-197 20 80 1-225 20 80 1-226 20 80 2-196 20 80 1-207 20 80 2-32 20 90 2-33 20 80 2-42 20 80 2-288 20 80 1-212 20 80 2-291 20 80 1-164 20 100 2-276 20 80 1-211 20 80 1-274 20 80 1-341 20 80 1-343 20 80 1-345 20 80 1-346 20 80 2-345 20 80 1-195 20 80 2-349 20 90 2-92 20 80 2-90 20 80

TABLE 4b Pre-emergence action at 80 g/ha against AVEFA in % Example number Dosage [g/ha] AVEFA 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 90 3-338 80 90 2-337 80 100 3-337 80 100 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 80 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 90 2-125 80 100 3-125 80 80 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 90 2-81 80 80 2-82 80 100 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 90 1-149 80 100 2-149 80 100 6-124 80 90 5-59 80 80 5-58 80 80 5-117 80 90 5-74 80 80 1-82 80 90 1-87 80 90 2-87 80 90 1-88 80 90 2-88 80 90 1-209 80 100 1-4 80 90 1-25 80 90 2-25 80 100 3-27 80 90 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 90 3-273 80 90 1-44 80 90 2-44 80 90 1-45 80 90 2-45 80 100 1-46 80 100 2-46 80 100 1-30 80 100 2-30 80 100 1-31 80 90 2-31 80 100 1-28 80 100 2-28 80 90 1-29 80 90 2-29 80 100 1-306 80 80 1-177 80 100 2-177 80 90 1-178 80 100 2-178 80 100 6-141 80 80 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 90 1-135 80 100 2-135 80 90 6-254 80 90 1-134 80 90 2-134 80 90 1-133 80 100 2-133 80 90 6-120 80 90 1-277 80 90 1-278 80 90 2-278 80 90 1-279 80 90 2-279 80 100 2-195 80 80 2-225 80 80 1-197 80 100 2-227 80 90 1-227 80 90 2-197 80 100 1-225 80 80 1-226 80 90 2-226 80 100 2-196 80 100 1-56 80 80 2-57 80 90 1-58 80 80 2-58 80 90 1-57 80 90 1-207 80 90 2-207 80 90 2-32 80 90 2-34 80 90 6-255 80 80 2-33 80 90 2-42 80 90 6-256 80 80 2-73 80 80 2-74 80 80 1-137 80 90 1-136 80 80 1-180 80 80 2-180 80 80 1-183 80 90 2-183 80 80 1-182 80 90 2-182 80 90 1-181 80 80 2-181 80 90 1-228 80 90 2-228 80 80 1-230 80 90 2-230 80 80 2-287 80 80 2-288 80 90 1-210 80 90 2-210 80 90 1-212 80 90 2-212 80 90 1-288 80 90 1-289 80 80 2-291 80 80 2-292 80 90 1-271 80 80 2-47 80 80 1-339 80 100 2-339 80 80 2-49 80 80 1-229 80 80 2-229 80 90 1-340 80 80 1-33 80 100 1-155 80 90 2-155 80 90 1-164 80 100 1-166 80 100 2-211 80 80 2-272 80 80 2-276 80 90 1-276 80 90 1-211 80 90 1-274 80 90 6-168 80 80 1-272 80 90 6-211 80 80 1-341 80 90 2-341 80 90 1-83 80 80 2-83 80 90 1-89 80 90 2-89 80 90 1-342 80 100 1-343 80 80 2-342 80 90 1-344 80 90 2-343 80 100 1-345 80 90 2-344 80 80 1-346 80 80 2-345 80 80 2-346 80 80 1-195 80 90 2-184 80 90 1-185 80 100 2-185 80 100 2-186 80 80 1-349 80 100 1-350 80 90 2-348 80 100 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 100 1-352 80 80 1-86 80 100 2-86 80 90 2-92 80 80 2-90 80 90 2-351 80 80 2-352 80 80 2-354 80 90

TABLE 4c Pre-emergence action at 320 g/ha against AVEFA in % Example number Dosage [g/ha] AVEFA 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320  90 2-337 320 100 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 5a Pre-emergence action at 20 g/ha against CYPES in % Example number Dosage [g/ha] CYPES 2-129 20 100 1-129 20 90 6-116 20 100 6-253 20 80

TABLE 5b Pre-emergence action at 80 g/ha against CYPES in % Example number Dosage [g/ha] CYPES 3-129 80 100 2-129 80 100 1-129 80 90 6-116 80 100 1-338 80 90 2-338 80 90 3-338 80 90 6-253 80 90

TABLE 5c Pre-emergence action at 320 g/ha against CYPES in % Example number Dosage [g/ha] CYPES 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 90 6-253 320 100

TABLE 6a Pre-emergence action at 20 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 1-129 20 80 2-337 20 80 1-26 20 80 1-130 20 90 2-130 20 80 6-124 20 80 5-59 20 80 5-117 20 80 5-123 20 90 5-122 20 80 2-87 20 80 1-88 20 90 2-27 20 90 1-273 20 90 1-31 20 90 2-28 20 80 1-305 20 80 2-305 20 80 1-177 20 80 1-178 20 80 1-132 20 90 1-135 20 80 6-254 20 90 2-134 20 80 1-278 20 90 1-227 20 80 1-225 20 90 1-226 20 80 2-226 20 100 2-57 20 90 1-58 20 100 1-57 20 90 2-42 20 90 6-256 20 80 1-137 20 80 1-183 20 90 1-228 20 90 2-287 20 90 2-288 20 90 1-210 20 80 2-210 20 80 1-288 20 80 1-289 20 80 1-271 20 90 1-32 20 80 1-164 20 100 1-166 20 90 1-211 20 90 6-161 20 80 1-345 20 90 2-344 20 90 2-84 20 90 2-350 20 80 1-86 20 90 2-86 20 80 2-90 20 90 1-353 20 90

TABLE 6b Pre-emergence action at 80 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 3-129 80 80 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 90 2-337 80 100 3-337 80 90 1-26 80 100 2-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 80 6-159 80 100 1-130 80 100 2-130 80 100 6-117 80 90 1-81 80 100 2-81 80 100 2-82 80 100 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 90 6-124 80 100 5-59 80 100 5-58 80 90 5-117 80 100 5-75 80 100 5-74 80 90 5-123 80 100 5-122 80 100 1-82 80 100 1-87 80 100 2-87 80 100 1-88 80 100 2-88 80 100 1-209 80 90 1-4 80 90 1-25 80 100 2-25 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 90 3-273 80 80 6-212 80 90 4-212 80 80 1-44 80 90 1-45 80 90 2-45 80 100 6-32 80 90 1-46 80 80 2-46 80 90 6-33 80 100 1-30 80 80 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 90 2-29 80 100 1-304 80 100 2-304 80 90 1-305 80 100 2-305 80 100 1-306 80 100 2-306 80 100 1-177 80 100 2-177 80 90 1-178 80 100 2-178 80 100 6-141 80 90 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 100 1-134 80 100 2-134 80 100 1-133 80 100 2-133 80 100 6-120 80 100 1-277 80 90 2-277 80 90 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 80 2-225 80 90 1-197 80 90 2-227 80 100 1-227 80 90 2-197 80 100 1-225 80 100 1-226 80 100 2-226 80 100 6-165 80 100 6-166 80 80 1-56 80 90 6-45 80 80 6-44 80 100 2-57 80 100 6-43 80 100 1-58 80 100 2-58 80 100 2-56 80 90 1-57 80 90 1-207 80 90 2-207 80 100 2-271 80 100 6-210 80 90 2-32 80 100 1-34 80 90 2-34 80 90 6-255 80 100 2-33 80 100 2-42 80 100 6-256 80 100 1-146 80 100 1-141 80 90 1-37 80 80 2-37 80 80 1-72 80 80 2-72 80 100 1-73 80 100 2-73 80 100 1-74 80 100 2-74 80 100 1-144 80 100 2-144 80 80 1-138 80 100 2-138 80 90 2-141 80 80 1-137 80 100 1-136 80 90 1-180 80 100 2-180 80 100 1-183 80 100 2-183 80 90 6-257 80 80 1-182 80 100 2-182 80 100 6-145 80 90 1-181 80 100 2-181 80 100 6-144 80 100 1-228 80 100 2-228 80 100 6-167 80 100 1-230 80 90 2-230 80 90 6-169 80 90 2-286 80 90 1-287 80 90 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 90 2-213 80 90 1-288 80 100 1-289 80 100 2-289 80 100 6-228 80 90 1-291 80 90 2-291 80 90 6-230 80 80 2-292 80 100 1-271 80 100 2-47 80 100 6-34 80 100 1-339 80 100 2-339 80 100 6-258 80 100 1-49 80 80 2-49 80 90 1-229 80 80 2-229 80 80 1-340 80 100 6-267 80 80 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 100 1-155 80 100 2-155 80 100 6-260 80 100 1-164 80 100 2-164 80 80 6-261 80 100 1-165 80 100 1-166 80 100 1-156 80 100 2-156 80 100 6-262 80 90 1-159 80 90 2-159 80 90 1-162 80 100 2-162 80 80 2-211 80 90 2-272 80 100 2-276 80 80 1-276 80 100 1-211 80 100 1-274 80 100 6-168 80 90 1-272 80 100 6-211 80 100 1-341 80 90 1-292 80 90 2-341 80 100 1-83 80 90 2-83 80 90 6-60 80 80 1-89 80 100 2-89 80 90 6-161 80 100 1-342 80 100 1-343 80 90 2-342 80 80 1-344 80 90 2-343 80 90 1-345 80 100 2-344 80 100 1-346 80 90 2-345 80 90 2-346 80 90 1-195 80 100 1-184 80 100 2-184 80 100 1-185 80 100 2-185 80 90 1-186 80 80 2-186 80 100 1-349 80 90 1-350 80 100 2-348 80 100 1-351 80 100 2-349 80 90 1-84 80 100 2-84 80 100 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 100 1-92 80 100 2-92 80 100 1-90 80 100 2-90 80 100 1-353 80 100 2-351 80 100 2-352 80 80

TABLE 6c Pre-emergence action at 320 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 100 6-252 320 90 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 7a Pre-emergence action at 20 g/ha against HORMU in % Example number Dosage [g/ha] HORMU 2-337 20 90 2-130 20 90

TABLE 7b Pre-emergence action at 80 g/ha against HORMU in % Example number Dosage [g/ha] HORMU 3-129 80 90 2-129 80 90 1-129 80 90 6-116 80 90 2-338 80 80 3-338 80 80 2-337 80 90 3-337 80 100 1-26 80 80 2-26 80 90 3-26 80 80 6-26 80 80 1-208 80 80 2-208 80 90 6-159 80 80 1-130 80 90 2-130 80 100 1-81 80 80 2-81 80 90 2-82 80 80 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90 1-131 80 80 2-131 80 80 1-149 80 90 2-149 80 90 6-124 80 80 5-117 80 80 2-87 80 80 2-88 80 80 1-209 80 80 1-4 80 80 2-25 80 90 1-27 80 80 2-27 80 90 1-173 80 90 2-173 80 100 1-273 80 80 2-273 80 80 2-46 80 90

TABLE 7c Pre-emergence action at 320 g/ha against HORMU in % Example number Dosage [g/ha] HORMU 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 90 2-337 320 100 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 90 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 8a Pre-emergence action at 20 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI 1-173 20 80 1-164 20 100

TABLE 8b Pre-emergence action at 80 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI 1-129 80 90 2-337 80 80 1-26 80 80 2-208 80 80 1-130 80 100 2-130 80 100 1-131 80 80 1-149 80 90 2-149 80 90 5-117 80 80 1-82 80 80 1-87 80 80 2-87 80 80 2-88 80 80 1-25 80 80 2-25 80 80 1-27 80 80 2-27 80 80 1-173 80 90 2-173 80 90 1-273 80 80 2-273 80 80 1-45 80 80 2-45 80 80 1-46 80 90 2-46 80 90 1-177 80 90 2-177 80 90 1-178 80 80 2-178 80 80 1-179 80 90 2-179 80 80 1-132 80 80 2-132 80 90 2-135 80 80 1-134 80 80 2-134 80 80 2-133 80 80 2-279 80 80 2-195 80 90 1-197 80 80 1-227 80 90 2-197 80 90 1-225 80 80 2-196 80 100 2-32 80 90 1-34 80 80 6-255 80 80 2-33 80 80 2-42 80 80 1-138 80 90 1-137 80 90 1-136 80 90 1-182 80 80 2-182 80 80 1-181 80 80 2-288 80 90 1-212 80 80 2-212 80 90 1-288 80 80 1-289 80 80 1-271 80 100 2-47 80 80 1-339 80 100 2-339 80 80 1-47 80 80 1-33 80 80 1-32 80 90 2-154 80 90 1-155 80 90 2-155 80 80 1-164 80 100 1-165 80 80 1-166 80 80 1-159 80 80 2-276 80 80 1-272 80 80 1-83 80 80 1-343 80 80 2-342 80 80 1-344 80 90 2-343 80 90 1-345 80 80 1-195 80 80 2-184 80 80 1-185 80 90 1-349 80 90 1-92 80 90

TABLE 8c Pre-emergence action at 320 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 90 2-338 320 100 2-337 320 90 1-81 320 80 2-81 320 90 2-82 320 90 1-147 320 100 2-147 320 90 1-148 320 90 2-148 320 90

TABLE 9a Pre-emergence action at 20 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 3-129 20 90 2-129 20 100 1-129 20 100 6-116 20 90 2-337 20 80 1-123 20 80 2-123 20 80 1-26 20 100 2-26 20 100 3-26 20 90 6-26 20 80 1-208 20 90 2-208 20 100 3-208 20 100 6-159 20 100 1-125 20 80 2-125 20 80 3-125 20 100 1-130 20 100 2-130 20 100 1-131 20 100 2-131 20 90 6-118 20 90 1-149 20 100 2-149 20 90 6-124 20 90 5-59 20 80 5-58 20 90 5-117 20 90 5-75 20 80 5-74 20 80 1-82 20 100 1-87 20 80 2-87 20 90 1-88 20 100 2-88 20 100 1-209 20 80 1-25 20 90 2-25 20 100 3-27 20 100 1-27 20 100 2-27 20 100 1-173 20 80 2-173 20 100 1-273 20 100 2-273 20 100 3-273 20 90 6-212 20 80 4-212 20 80 1-44 20 90 2-44 20 90 1-45 20 100 2-45 20 90 1-46 20 90 2-46 20 90 6-33 20 80 1-30 20 100 2-30 20 100 1-31 20 100 2-31 20 100 1-28 20 100 2-28 20 100 1-29 20 100 2-29 20 100 1-304 20 90 2-304 20 90 1-305 20 100 2-305 20 100 1-306 20 100 2-306 20 90 1-177 20 90 2-177 20 90 1-178 20 90 2-178 20 90 1-179 20 90 2-179 20 100 1-132 20 100 2-132 20 100 1-135 20 90 2-135 20 90 6-254 20 80 1-134 20 90 2-134 20 90 1-133 20 90 2-133 20 90 6-120 20 90 1-277 20 90 2-277 20 90 1-278 20 100 2-278 20 100 1-279 20 100 2-279 20 90 2-195 20 100 2-225 20 80 1-197 20 90 2-227 20 100 1-227 20 80 2-197 20 80 1-225 20 90 1-226 20 100 2-226 20 90 6-165 20 80 2-196 20 100 1-56 20 90 2-57 20 90 1-58 20 90 2-58 20 100 2-56 20 90 1-57 20 90 1-207 20 90 2-207 20 90 2-271 20 100 6-210 20 80 2-32 20 100 2-34 20 90 2-33 20 100 2-42 20 100 2-146 20 100 2-142 20 80 1-143 20 80 5-255 20 80 1-146 20 100 2-143 20 90 1-72 20 80 2-72 20 100 1-73 20 90 2-73 20 100 1-74 20 100 2-74 20 100 1-144 20 90 1-138 20 90 2-138 20 90 2-141 20 80 1-137 20 100 1-136 20 90 1-180 20 90 2-180 20 100 1-183 20 90 2-183 20 90 6-257 20 80 1-182 20 90 2-182 20 90 1-181 20 90 2-181 20 90 1-228 20 80 2-228 20 90 1-230 20 90 2-230 20 90 2-286 20 100 1-287 20 100 2-287 20 100 2-288 20 90 1-210 20 100 2-210 20 100 1-212 20 90 2-213 20 100 1-288 20 100 1-289 20 90 2-289 20 90 1-291 20 90 2-291 20 90 2-292 20 90 1-271 20 100 2-47 20 100 2-339 20 100 1-49 20 90 2-49 20 100 1-229 20 100 2-229 20 100 1-340 20 100 6-267 20 90 2-340 20 100 1-47 20 80 1-33 20 100 1-32 20 100 2-154 20 100 6-259 20 90 1-155 20 100 2-155 20 100 6-260 20 100 2-164 20 100 6-261 20 90 1-165 20 100 1-166 20 100 1-156 20 90 2-156 20 100 2-161 20 80 2-211 20 90 2-272 20 100 1-161 20 90 2-276 20 100 1-276 20 90 1-211 20 90 1-274 20 100 6-168 20 80 1-272 20 90 1-341 20 100 1-292 20 100 2-341 20 100 1-83 20 90 2-83 20 100 1-89 20 90 2-89 20 90 6-161 20 100 1-342 20 80 2-342 20 90 1-344 20 90 2-343 20 80 1-345 20 100 2-344 20 100 1-346 20 90 2-345 20 100 2-346 20 90 1-195 20 90 1-184 20 80 2-184 20 90 1-185 20 100 2-185 20 100 2-186 20 80 2-348 20 90 2-349 20 90 1-84 20 100 2-84 20 100 1-352 20 100 2-350 20 100 1-86 20 100 2-86 20 100 1-92 20 100 2-92 20 100 1-90 20 100 2-90 20 100 1-353 20 100 2-351 20 100 1-354 20 80 2-352 20 90 1-355 20 80 2-353 20 90 2-354 20 100

TABLE 9b Pre-emergence action at 80 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 90 1-338 80 80 2-338 80 90 3-338 80 90 2-337 80 100 3-337 80 100 1-123 80 100 2-123 80 100 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 90 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 100 1-125 80 100 2-125 80 100 3-125 80 100 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 100 2-81 80 100 2-82 80 100 6-58 80 80 1-147 80 90 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 100 6-124 80 100 5-59 80 90 5-58 80 100 5-117 80 100 5-75 80 100 5-74 80 90 5-122 80 90 1-82 80 100 1-87 80 90 2-87 80 90 1-88 80 100 2-88 80 100 1-209 80 100 1-4 80 100 1-25 80 100 2-25 80 100 3-27 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 100 3-273 80 100 6-212 80 90 4-212 80 80 4-212 80 90 1-44 80 90 2-44 80 100 1-45 80 100 2-45 80 100 6-32 80 90 1-46 80 100 2-46 80 100 6-33 80 90 1-30 80 100 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 100 2-29 80 100 1-304 80 100 2-304 80 100 6-231 80 80 1-305 80 100 2-305 80 100 1-306 80 100 2-306 80 100 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 6-141 80 80 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 100 1-134 80 100 2-134 80 100 1-133 80 100 2-133 80 100 6-120 80 90 1-277 80 100 2-277 80 100 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 100 1-225 80 100 1-226 80 100 2-226 80 100 6-165 80 100 6-166 80 100 2-196 80 100 1-56 80 90 6-45 80 90 6-44 80 80 2-57 80 100 6-43 80 80 1-58 80 100 2-58 80 100 2-56 80 100 1-57 80 100 1-207 80 100 2-207 80 100 2-271 80 100 6-210 80 90 2-32 80 100 1-34 80 90 2-34 80 100 6-255 80 100 2-33 80 100 2-42 80 100 6-256 80 90 2-146 80 100 2-142 80 100 1-143 80 100 5-255 80 100 1-142 80 90 1-146 80 100 1-141 80 100 1-37 80 90 2-143 80 100 1-72 80 100 2-72 80 100 1-73 80 100 2-73 80 100 6-50 80 80 1-74 80 100 2-74 80 100 2-35 80 80 1-144 80 90 2-144 80 90 1-138 80 100 2-138 80 100 2-141 80 90 1-137 80 100 1-136 80 100 1-180 80 100 2-180 80 100 1-183 80 100 2-183 80 100 6-257 80 90 1-182 80 100 2-182 80 100 1-181 80 100 2-181 80 100 6-144 80 80 2-36 80 90 1-228 80 100 2-228 80 100 6-167 80 90 1-230 80 100 2-230 80 100 6-169 80 80 2-286 80 100 1-287 80 100 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 100 2-213 80 100 1-288 80 100 1-289 80 100 2-289 80 100 6-228 80 80 1-291 80 100 2-291 80 100 6-230 80 80 2-292 80 100 1-271 80 100 2-47 80 100 6-34 80 90 1-339 80 100 2-339 80 100 6-258 80 90 1-49 80 100 2-49 80 100 1-41 80 100 1-229 80 100 2-229 80 100 1-340 80 100 6-267 80 100 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 100 1-155 80 100 2-155 80 100 6-260 80 100 1-164 80 100 2-164 80 100 6-261 80 100 1-165 80 100 1-166 80 100 1-156 80 100 2-156 80 100 6-262 80 100 1-159 80 90 2-159 80 90 1-162 80 90 2-162 80 90 1-160 80 80 2-160 80 90 2-161 80 90 6-266 80 80 2-211 80 100 2-272 80 100 1-161 80 100 2-276 80 100 1-276 80 100 1-211 80 100 1-274 80 100 6-168 80 90 1-272 80 100 6-211 80 90 1-341 80 100 1-292 80 100 2-341 80 100 2-158 80 90 1-83 80 100 2-83 80 100 6-60 80 90 1-89 80 100 2-89 80 100 6-76 80 90 6-161 80 100 1-342 80 100 1-343 80 100 2-342 80 100 1-344 80 100 2-343 80 100 1-345 80 100 2-344 80 100 1-346 80 100 2-345 80 100 1-347 80 90 2-346 80 90 1-195 80 100 1-184 80 100 2-184 80 100 1-185 80 100 2-185 80 100 1-186 80 90 2-186 80 100 1-349 80 90 1-350 80 90 2-348 80 90 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 100 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 100 1-92 80 100 2-92 80 100 1-90 80 100 2-90 80 100 1-353 80 100 2-351 80 100 1-354 80 80 2-352 80 90 1-355 80 100 2-353 80 100 1-356 80 100 2-354 80 100

TABLE 9c Pre-emergence action at 320 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 100 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 10a Pre-emergence action at 20 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 3-129 20 80 2-26 20 90 2-27 20 80 2-134 20 80 1-277 20 80 2-279 20 80 2-197 20 80 2-196 20 80 1-56 20 80 1-57 20 80 2-33 20 80 2-42 20 80 1-138 20 80 1-137 20 80 2-287 20 80 2-210 20 80 1-212 20 80 2-213 20 80 2-291 20 80 2-292 20 80 1-271 20 80 1-339 20 100 2-154 20 80 2-86 20 80

TABLE 10b Pre-emergence action at 80 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 3-129 80 90 2-129 80 90 1-129 80 90 3-337 80 90 2-26 80 100 2-131 80 80 2-149 80 80 5-59 80 80 5-117 80 100 1-82 80 80 1-87 80 80 2-87 80 80 1-88 80 90 2-88 80 90 1-209 80 80 1-25 80 90 2-25 80 80 3-27 80 90 1-27 80 100 2-27 80 90 1-173 80 90 2-173 80 90 1-273 80 100 2-273 80 90 3-273 80 90 1-44 80 80 1-45 80 90 2-45 80 80 1-46 80 80 2-46 80 90 1-30 80 100 2-30 80 80 1-31 80 80 2-31 80 80 2-29 80 80 1-304 80 80 2-304 80 90 1-305 80 90 2-305 80 90 1-306 80 90 2-306 80 100 1-177 80 80 2-177 80 80 1-178 80 80 2-179 80 80 1-132 80 80 2-132 80 90 1-135 80 80 2-135 80 80 1-134 80 80 2-134 80 90 2-133 80 80 6-120 80 80 1-277 80 90 2-277 80 80 1-278 80 90 2-278 80 90 1-279 80 90 2-279 80 90 2-225 80 90 2-227 80 90 1-227 80 80 2-197 80 90 1-225 80 100 2-226 80 100 2-196 80 90 1-56 80 80 2-57 80 80 1-58 80 90 2-58 80 90 2-56 80 80 1-57 80 80 1-207 80 80 2-207 80 80 2-271 80 100 2-32 80 90 2-34 80 80 6-255 80 90 2-33 80 80 2-42 80 90 6-256 80 80 2-146 80 90 1-146 80 80 1-141 80 80 2-37 80 80 2-73 80 80 1-74 80 100 2-74 80 90 1-138 80 90 2-138 80 80 2-141 80 80 1-137 80 90 1-136 80 80 2-180 80 100 1-183 80 90 2-183 80 90 1-182 80 90 2-182 80 90 1-181 80 80 2-181 80 80 1-228 80 90 2-228 80 100 1-230 80 90 2-230 80 80 2-286 80 90 1-287 80 100 2-287 80 80 2-288 80 90 1-210 80 80 2-210 80 90 1-212 80 80 2-212 80 80 2-213 80 90 1-288 80 100 1-289 80 80 2-289 80 80 6-228 80 80 1-291 80 80 2-291 80 90 2-292 80 90 1-271 80 90 2-47 80 90 1-339 80 100 2-339 80 80 6-258 80 90 2-49 80 80 1-229 80 90 1-340 80 90 2-340 80 80 1-33 80 100 1-32 80 80 2-154 80 100 6-259 80 80 1-155 80 100 2-155 80 100 1-164 80 100 2-164 80 100 1-165 80 100 1-166 80 80 1-156 80 80 2-159 80 90 2-272 80 80 1-161 80 80 2-276 80 90 1-276 80 90 1-211 80 80 1-274 80 90 1-272 80 80 1-341 80 80 1-292 80 80 2-341 80 80 1-89 80 80 2-344 80 90 2-345 80 80 1-184 80 80 2-184 80 90 1-185 80 80 2-185 80 100 1-186 80 80 2-348 80 80 2-84 80 90 1-86 80 80 2-86 80 90 1-92 80 90 2-92 80 90 2-351 80 80

TABLE 10c Pre-emergence action at 320 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 80 1-338 320 80 2-338 320 80 3-338 320 100 2-337 320 90

TABLE 11a Pre-emergence action at 20 g/ha against POLCO in % Example Dosage number [g/ha] POLCO 2-129 20 100 1-337 20 80 3-26 20 80 1-208 20 80 1-125 20 80 5-74 20 80 2-25 20 100 2-27 20 80 2-173 20 90 2-44 20 80 1-45 20 90 2-30 20 80 2-31 20 80 1-278 20 90 2-278 20 80 1-279 20 80 2-279 20 80 1-58 20 80 2-146 20 80 2-72 20 80 2-144 20 80 1-137 20 80 2-183 20 90 1-166 20 100 1-276 20 80 1-274 20 80 1-272 20 80

TABLE 11b Pre-emergence action at 80 g/ha against POLCO in % Example Dosage number [g/ha] POLCO 3-129 80 80 2-129 80 100 1-129 80 100 3-338 80 80 1-337 80 80 2-123 80 80 1-26 80 90 2-26 80 80 3-26 80 90 6-26 80 100 1-208 80 90 2-208 80 90 3-208 80 80 6-159 80 80 1-125 80 80 1-131 80 80 2-131 80 90 6-118 80 80 1-149 80 80 2-149 80 100 5-117 80 80 5-74 80 80 5-123 80 80 1-82 80 90 1-87 80 90 1-88 80 80 2-88 80 90 1-25 80 80 2-25 80 100 2-27 80 100 1-173 80 80 2-173 80 100 1-273 80 90 2-44 80 90 1-45 80 90 2-45 80 90 6-32 80 80 1-46 80 80 2-46 80 90 2-30 80 80 2-31 80 80 2-28 80 90 1-304 80 80 2-304 80 80 1-305 80 80 1-306 80 90 2-306 80 80 1-132 80 80 2-132 80 80 1-277 80 90 2-277 80 90 1-278 80 100 2-278 80 80 1-279 80 90 2-279 80 90 2-195 80 80 2-225 80 90 1-227 80 90 2-197 80 100 1-225 80 90 1-226 80 90 2-226 80 80 6-165 80 80 6-166 80 80 2-196 80 90 1-56 80 90 2-57 80 90 1-58 80 90 2-58 80 80 2-56 80 90 1-207 80 90 2-207 80 90 2-271 80 80 2-32 80 90 2-34 80 90 2-42 80 80 2-146 80 80 1-146 80 80 2-72 80 80 2-73 80 80 1-74 80 80 2-74 80 80 2-35 80 80 2-144 80 90 1-138 80 90 2-138 80 90 2-141 80 80 1-137 80 100 1-180 80 100 2-180 80 90 1-183 80 80 2-183 80 90 2-182 80 90 6-169 80 100 2-287 80 80 2-288 80 90 1-212 80 80 2-212 80 80 1-288 80 80 1-289 80 80 2-289 80 80 1-291 80 80 2-291 80 80 2-292 80 100 1-271 80 80 2-47 80 80 1-339 80 80 2-339 80 80 6-258 80 80 1-49 80 90 2-49 80 90 1-229 80 80 1-340 80 90 1-47 80 100 1-33 80 90 1-32 80 100 2-154 80 90 6-259 80 90 1-155 80 90 2-155 80 90 2-164 80 90 1-165 80 90 1-166 80 100 2-156 80 90 2-272 80 80 1-161 80 80 2-276 80 90 1-276 80 90 1-211 80 90 1-274 80 90 1-272 80 90 6-211 80 90 1-341 80 80 1-292 80 90 2-83 80 90 1-89 80 80 2-342 80 80 2-343 80 90 1-345 80 90 2-344 80 90 1-346 80 80 2-345 80 90 1-184 80 80 2-348 80 90 2-350 80 100 1-86 80 80 1-354 80 80 1-355 80 80

TABLE 11c Pre-emergence action at 320 g/ha against POLCO in % Example Dosage number [g/ha] POLCO 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 90 1-338 320 80 2-338 320 90 3-338 320 80 2-337 320 80 2-81 320 100 2-82 320 90 1-147 320 90 2-147 320 80 1-148 320 80 2-148 320 100

TABLE 12a Pre-emergence action at 20 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 2-129 20 100 2-337 20 90 1-26 20 80 2-26 20 80 1-208 20 100 2-208 20 80 1-130 20 90 2-130 20 90 1-131 20 80 2-131 20 80 1-149 20 90 6-124 20 80 1-82 20 80 1-209 20 90 1-25 20 80 2-25 20 100 1-27 20 100 1-173 20 90 1-273 20 100 2-273 20 80 1-30 20 90 2-30 20 100 1-304 20 90 1-305 20 80 2-177 20 100 1-179 20 80 1-132 20 80 1-134 20 90 2-134 20 80 2-133 20 100 1-279 20 80 2-279 20 80 2-195 20 80 1-197 20 100 2-227 20 100 2-197 20 90 1-225 20 90 1-226 20 100 2-226 20 80 6-165 20 90 2-196 20 90 1-56 20 90 2-57 20 80 1-58 20 100 2-58 20 100 2-56 20 100 1-57 20 90 1-207 20 100 2-207 20 100 2-271 20 100 2-32 20 100 2-34 20 100 6-255 20 100 2-33 20 80 2-42 20 80 6-256 20 80 1-141 20 90 1-37 20 90 1-74 20 100 2-141 20 90 1-182 20 100 2-182 20 90 6-167 20 80 1-230 20 90 2-286 20 80 1-287 20 90 2-287 20 90 2-288 20 90 1-212 20 80 1-288 20 100 1-340 20 90 1-155 20 80 1-166 20 80 1-272 20 80 1-341 20 80 1-89 20 90 1-346 20 100 1-195 20 90 1-349 20 90 1-351 20 100 1-86 20 80 2-92 20 100

TABLE 12b Pre-emergence action at 80 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 3-129 80 90 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 90 1-337 80 90 2-337 80 100 6-252 80 90 1-26 80 100 2-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 100 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 100 2-81 80 100 2-82 80 100 6-58 80 100 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 100 6-124 80 100 5-59 80 100 5-58 80 100 5-117 80 90 5-253 80 80 5-75 80 100 5-74 80 90 5-123 80 100 5-122 80 100 1-82 80 100 1-87 80 100 2-87 80 100 1-88 80 100 2-88 80 100 1-209 80 100 1-4 80 100 1-25 80 100 2-25 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 90 3-273 80 100 6-212 80 90 1-44 80 100 2-44 80 100 1-45 80 100 2-45 80 100 1-46 80 100 2-46 80 100 6-33 80 100 1-30 80 100 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 100 2-29 80 100 1-304 80 100 2-304 80 90 1-305 80 100 2-305 80 80 1-306 80 100 2-306 80 100 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 80 1-134 80 100 2-134 80 100 1-133 80 100 2-133 80 100 6-120 80 100 1-277 80 100 2-277 80 80 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 100 1-225 80 100 1-226 80 100 2-226 80 100 6-165 80 100 6-166 80 100 2-196 80 100 1-56 80 100 6-45 80 100 6-44 80 90 2-57 80 100 6-43 80 90 1-58 80 100 2-58 80 100 2-56 80 100 1-57 80 100 1-207 80 100 2-207 80 100 2-271 80 100 6-210 80 100 2-32 80 100 1-34 80 100 2-34 80 100 6-255 80 100 2-33 80 100 2-42 80 100 6-256 80 100 2-146 80 100 1-146 80 80 1-141 80 100 1-37 80 100 2-37 80 100 1-72 80 100 2-72 80 100 1-73 80 100 2-73 80 100 1-74 80 100 2-74 80 100 1-144 80 80 1-138 80 100 2-138 80 80 2-141 80 100 1-137 80 100 1-136 80 80 1-180 80 90 2-180 80 100 1-183 80 100 2-183 80 100 1-182 80 100 2-182 80 100 6-145 80 100 1-181 80 100 2-181 80 100 6-144 80 90 1-228 80 100 2-228 80 90 6-167 80 80 1-230 80 100 2-230 80 90 6-169 80 100 2-286 80 100 1-287 80 100 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 100 2-213 80 100 1-288 80 100 1-289 80 80 2-289 80 90 6-228 80 80 1-291 80 100 2-291 80 100 2-292 80 100 1-271 80 100 2-47 80 100 2-339 80 100 6-258 80 80 1-49 80 80 2-49 80 100 1-229 80 100 2-229 80 100 1-340 80 100 6-267 80 80 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 100 1-155 80 100 2-155 80 90 6-260 80 100 2-164 80 80 6-261 80 100 1-165 80 100 1-166 80 100 1-156 80 100 2-156 80 100 6-262 80 100 1-162 80 80 6-264 80 80 2-211 80 100 2-272 80 100 2-276 80 100 1-276 80 100 1-211 80 100 1-274 80 100 6-168 80 90 1-272 80 100 6-211 80 100 1-341 80 100 1-292 80 100 2-341 80 90 1-83 80 100 2-83 80 100 1-89 80 100 2-89 80 100 6-76 80 80 6-161 80 100 1-343 80 100 2-342 80 100 1-344 80 100 2-343 80 100 1-345 80 100 2-344 80 80 1-346 80 100 2-345 80 100 1-195 80 100 1-185 80 100 2-185 80 100 1-186 80 80 1-349 80 100 1-350 80 100 2-348 80 100 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 100 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 100 1-92 80 100 2-92 80 100 1-90 80 100 2-90 80 100 1-353 80 100 2-351 80 100 1-354 80 90 2-352 80 100 1-355 80 90

TABLE 12c Pre-emergence action at 320 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 100 6-252 320 90 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 13a Pre-emergence action at 20 g/ha against STEME in % Example Dosage number [g/ha] STEME 3-129 20 90 2-129 20 80 1-129 20 100 6-116 20 90 2-337 20 90 1-26 20 100 2-26 20 100 3-26 20 80 6-26 20 80 1-208 20 100 2-208 20 100 3-208 20 90 6-159 20 80 2-125 20 80 3-125 20 90 1-130 20 100 2-130 20 100 1-131 20 100 2-131 20 100 6-118 20 90 1-149 20 90 2-149 20 100 6-124 20 80 5-59 20 90 5-58 20 100 5-117 20 90 5-75 20 100 5-74 20 90 5-123 20 90 5-122 20 90 1-82 20 100 1-87 20 90 2-87 20 100 1-88 20 100 2-88 20 100 1-25 20 80 2-25 20 90 3-27 20 100 1-27 20 90 2-27 20 100 1-173 20 80 2-173 20 100 1-273 20 100 2-273 20 90 3-273 20 90 6-212 20 80 1-44 20 90 2-44 20 90 1-45 20 90 2-45 20 90 1-46 20 90 2-46 20 90

TABLE 13b Pre-emergence action at 80 g/ha against STEME in % Example Dosage number [g/ha] STEME 3-129 80 100 2-129 80 80 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 90 3-338 80 90 2-337 80 90 3-337 80 100 1-123 80 90 2-123 80 80 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 100 1-125 80 100 2-125 80 100 3-125 80 100 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 100 2-81 80 90 2-82 80 100 6-58 80 90 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 90 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 100 6-124 80 90 5-59 80 100 5-58 80 100 5-117 80 90 5-253 80 90 5-75 80 100 5-74 80 100 5-123 80 90 5-122 80 90 1-82 80 100 1-87 80 100 2-87 80 100 1-88 80 100 2-88 80 100 1-209 80 90 1-4 80 90 1-25 80 90 2-25 80 100 3-27 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 90 3-273 80 100 6-212 80 90 4-212 80 90 1-44 80 90 2-44 80 100 1-45 80 90 2-45 80 100 6-32 80 90 1-46 80 100 2-46 80 100

TABLE 13c Pre-emergence action at 320 g/ha against STEME in % Example number Dosage [g/ha] STEME 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 90 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 100 6-252 320 90 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 90 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 14a Pre-emergence action at 20 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 2-337 20 80 1-125 20 80 1-209 20 90 1-4 20 80 1-25 20 80 1-27 20 80 2-27 20 80 1-178 20 80 2-56 20 80 2-32 20 90 2-34 20 90 2-33 20 80 6-256 20 80 2-37 20 80 1-73 20 80 2-73 20 90 1-183 20 90 2-286 20 80 2-287 20 90 2-292 20 90 1-271 20 90 1-339 20 100 2-339 20 80 6-258 20 90 1-340 20 100 1-32 20 80 2-155 20 80 1-165 20 80 1-166 20 80 2-156 20 80 1-161 20 80 1-274 20 90 1-341 20 80 1-292 20 100 1-158 20 80 2-158 20 80 2-342 20 80 1-344 20 80 1-349 20 90 1-84 20 80 2-84 20 80 1-352 20 90 1-356 20 100 2-354 20 80

TABLE 14b Pre-emergence action at 80 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 1-129 80 100 1-338 80 90 2-338 80 100 3-338 80 90 1-337 80 90 2-337 80 90 3-337 80 100 1-26 80 80 1-125 80 80 3-125 80 80 1-130 80 80 2-130 80 80 2-81 80 90 1-148 80 80 2-148 80 80 1-149 80 100 2-149 80 80 5-58 80 80 5-75 80 90 5-122 80 100 1-82 80 90 1-87 80 90 2-87 80 90 1-88 80 100 2-88 80 100 1-209 80 100 1-4 80 90 1-25 80 100 2-25 80 100 3-27 80 90 1-27 80 90 2-27 80 100 2-173 80 80 1-273 80 90 2-273 80 100 3-273 80 100 2-44 80 90 1-45 80 90 2-45 80 90 1-46 80 90 2-46 80 90 1-31 80 100 2-28 80 80 1-304 80 100 2-304 80 100 1-305 80 100 2-305 80 100 1-306 80 90 2-306 80 100 1-177 80 100 2-177 80 80 1-178 80 80 2-178 80 90 2-179 80 90 1-132 80 100 1-135 80 90 2-135 80 100 6-254 80 100 1-277 80 90 2-277 80 100 1-278 80 100 2-278 80 100 1-279 80 90 2-279 80 90 2-225 80 100 2-227 80 100 1-227 80 100 2-197 80 90 1-225 80 80 1-226 80 90 2-226 80 100 2-196 80 80 1-56 80 90 2-57 80 90 1-58 80 100 2-56 80 100 1-57 80 80 1-207 80 100 2-207 80 90 2-271 80 100 2-32 80 100 1-34 80 100 2-34 80 90 6-255 80 90 2-33 80 90 2-42 80 90 6-256 80 80 2-146 80 80 2-37 80 80 2-143 80 80 2-72 80 90 1-73 80 100 2-73 80 90 1-74 80 100 2-74 80 90 1-144 80 80 2-144 80 100 1-138 80 90 2-138 80 100 1-137 80 90 1-136 80 90 1-180 80 80 1-183 80 100 2-183 80 90 2-181 80 100 1-36 80 90 1-228 80 90 2-228 80 90 1-230 80 100 2-230 80 100 2-286 80 100 1-287 80 90 2-287 80 100 2-288 80 100 1-210 80 80 2-213 80 90 1-288 80 100 1-289 80 100 2-289 80 100 2-291 80 90 2-292 80 100 1-271 80 100 2-47 80 100 1-339 80 100 2-339 80 100 6-258 80 100 1-49 80 100 2-49 80 100 1-41 80 90 1-229 80 100 2-229 80 80 1-340 80 100 6-267 80 90 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 1-155 80 100 2-155 80 100 6-260 80 90 1-164 80 90 2-164 80 100 1-165 80 100 1-166 80 100 2-156 80 100 1-159 80 80 2-159 80 80 6-264 80 90 2-160 80 80 2-161 80 80 2-272 80 90 1-161 80 90 2-276 80 80 1-211 80 100 1-274 80 90 1-272 80 90 6-211 80 80 1-341 80 90 1-292 80 100 2-341 80 90 1-158 80 80 2-158 80 90 1-83 80 80 1-89 80 90 2-89 80 90 6-268 80 90 1-343 80 80 2-342 80 80 1-344 80 90 1-345 80 80 2-344 80 80 1-346 80 80 2-345 80 100 2-346 80 80 1-184 80 90 2-184 80 100 2-186 80 90 1-349 80 90 1-350 80 80 2-348 80 80 1-351 80 90 2-349 80 80 1-84 80 100 2-84 80 80 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 90 1-92 80 100 2-92 80 100 1-90 80 90 2-90 80 90 1-353 80 100 2-351 80 100 1-355 80 100 1-356 80 100 2-354 80 80

TABLE 14c Pre-emergence action at 320 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 80 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 90 6-117 320 90 1-81 320 100 2-81 320 90 2-82 320 90 1-147 320 90 2-147 320 90 1-148 320 100 2-148 320 100

TABLE 15a Pre-emergence action at 20 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 3-129 20 100 2-129 20 100 1-129 20 100 1-337 20 80 2-337 20 90 3-337 20 100 1-26 20 90 2-26 20 100 3-26 20 100 1-208 20 100 2-208 20 100 1-130 20 100 2-130 20 100 1-131 20 100 2-131 20 100 6-118 20 90 1-149 20 100 2-149 20 100 5-59 20 100 5-58 20 90 5-117 20 100 5-75 20 100 5-123 20 90 5-122 20 80 1-82 20 100 1-87 20 80 2-87 20 90 1-88 20 100 2-88 20 100 1-25 20 80 3-27 20 90 1-27 20 100 2-27 20 100 1-173 20 80 1-273 20 100 2-273 20 90 3-273 20 100 2-44 20 100 1-45 20 80 2-45 20 90 1-46 20 90 2-46 20 100 1-30 20 100 2-30 20 100 1-31 20 100 2-31 20 100 1-28 20 100 2-28 20 100 1-29 20 100 2-29 20 100 1-304 20 100 2-304 20 90 1-305 20 100 2-305 20 90 1-306 20 100 2-306 20 100 2-177 20 100 2-178 20 100 1-179 20 100 2-179 20 100 1-132 20 100 2-132 20 100 2-135 20 100 1-134 20 90 2-134 20 100 1-133 20 100 1-277 20 100 2-277 20 100 1-278 20 100 2-278 20 100 1-279 20 100 2-279 20 100 2-195 20 100 2-225 20 80 1-197 20 100 2-227 20 100 1-227 20 100 2-197 20 100 1-226 20 80 2-226 20 100 6-165 20 80 2-196 20 90 1-56 20 100 2-57 20 100 1-58 20 100 2-58 20 100 2-56 20 80 1-57 20 100 1-207 20 100 2-207 20 90 2-271 20 100 2-32 20 100 1-34 20 100 2-34 20 100 6-255 20 80 2-33 20 100 2-42 20 100 6-256 20 90 2-146 20 100 1-141 20 80 2-72 20 100 6-49 20 80 1-73 20 100 2-73 20 90 1-74 20 100 2-74 20 100 1-144 20 80 1-138 20 100 2-138 20 90 1-137 20 90 1-136 20 90 1-180 20 80 2-180 20 100 1-183 20 100 1-182 20 90 2-182 20 100 1-181 20 100 1-228 20 90 2-228 20 100 6-167 20 90 1-230 20 100 2-230 20 90 2-286 20 90 1-287 20 100 2-287 20 100 2-288 20 100 1-210 20 100 2-210 20 100 1-212 20 100 2-213 20 100 1-288 20 100 1-289 20 100 2-289 20 100 1-291 20 100 2-291 20 100 2-292 20 100 1-271 20 100 2-47 20 80 1-339 20 100 2-339 20 100 2-49 20 90 1-340 20 100 2-340 20 100 1-33 20 100 2-155 20 90 1-165 20 90 1-166 20 100 2-272 20 90 2-276 20 100 1-276 20 80 1-274 20 90 1-272 20 90 1-341 20 100 1-292 20 90 2-341 20 90 1-83 20 90 2-89 20 90 2-342 20 90 2-343 20 90 2-344 20 80 1-346 20 80 2-345 20 80 2-346 20 80 1-195 20 100 1-185 20 80 2-185 20 80 1-351 20 100 2-349 20 90 2-84 20 80 1-352 20 100 2-350 20 100 1-86 20 100 2-92 20 90 1-90 20 90 2-90 20 80 1-353 20 100 2-351 20 100 2-352 20 80 2-353 20 90 2-354 20 80

TABLE 15b Pre-emergence action at 80 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 80 2-338 80 100 3-338 80 90 1-337 80 80 2-337 80 100 3-337 80 100 1-123 80 80 2-123 80 80 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 100 6-159 80 100 1-125 80 100 2-125 80 100 3-125 80 100 1-130 80 100 2-130 80 100 6-117 80 80 1-81 80 90 2-81 80 90 2-82 80 100 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 90 1-149 80 100 2-149 80 100 6-124 80 100 5-59 80 100 5-58 80 100 5-117 80 100 5-253 80 90 5-75 80 100 5-74 80 100 5-123 80 100 5-122 80 100 1-82 80 100 1-87 80 100 2-87 80 90 1-88 80 100 2-88 80 100 1-209 80 100 1-25 80 100 2-25 80 100 3-27 80 100 1-27 80 100 2-27 80 100 1-173 80 90 2-173 80 100 1-273 80 100 2-273 80 100 3-273 80 100 4-212 80 90 1-44 80 90 2-44 80 100 1-45 80 100 2-45 80 100 1-46 80 100 2-46 80 100 6-33 80 100 1-30 80 100 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 100 2-29 80 100 1-304 80 100 2-304 80 100 1-305 80 100 2-305 80 100 1-306 80 100 2-306 80 100 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 90 1-134 80 100 2-134 80 100 1-133 80 100 2-133 80 90 6-120 80 90 1-277 80 100 2-277 80 100 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 100 1-225 80 100 1-226 80 100 2-226 80 100 6-165 80 90 6-166 80 100 2-196 80 100 1-56 80 100 6-45 80 90 2-57 80 100 1-58 80 100 2-58 80 100 2-56 80 90 1-57 80 100 1-207 80 100 2-207 80 100 2-271 80 100 6-210 80 90 2-32 80 100 1-34 80 100 2-34 80 100 6-255 80 90 2-33 80 100 2-42 80 100 6-256 80 90 2-146 80 100 2-142 80 100 5-255 80 100 1-142 80 90 5-254 80 90 1-140 80 90 1-146 80 100 1-141 80 100 1-37 80 100 2-37 80 100 2-143 80 80 1-72 80 100 2-72 80 100 6-49 80 80 1-73 80 100 2-73 80 100 1-74 80 100 2-74 80 100 1-144 80 100 2-144 80 90 1-138 80 100 2-138 80 100 2-141 80 90 1-137 80 100 1-136 80 100 1-180 80 100 2-180 80 100 1-183 80 100 2-183 80 100 1-182 80 100 2-182 80 100 1-181 80 100 2-181 80 80 2-36 80 100 1-228 80 100 2-228 80 100 6-167 80 100 1-230 80 100 2-230 80 100 2-286 80 100 1-287 80 100 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 100 2-213 80 100 1-288 80 100 1-289 80 100 2-289 80 100 1-291 80 100 2-291 80 100 2-292 80 100 1-271 80 100 2-47 80 100 1-339 80 100 2-339 80 100 6-258 80 80 1-49 80 100 2-49 80 100 1-41 80 100 1-229 80 100 2-229 80 100 1-340 80 100 6-267 80 80 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 80 1-155 80 100 2-155 80 100 2-164 80 100 1-165 80 100 1-166 80 100 1-156 80 100 2-156 80 100 6-262 80 90 2-159 80 80 2-162 80 80 1-160 80 80 2-160 80 100 2-161 80 100 2-211 80 80 2-272 80 100 2-276 80 100 1-276 80 100 1-211 80 100 1-274 80 90 1-272 80 100 6-211 80 80 1-341 80 100 1-292 80 100 2-341 80 100 1-158 80 90 2-158 80 100 1-83 80 100 2-83 80 100 1-89 80 100 2-89 80 100 6-161 80 80 1-343 80 100 2-342 80 100 1-344 80 100 2-343 80 100 1-345 80 100 2-344 80 100 1-346 80 100 2-345 80 100 1-347 80 80 2-346 80 80 1-195 80 100 1-184 80 90 2-184 80 100 1-185 80 100 2-185 80 100 2-186 80 90 1-349 80 100 1-350 80 100 2-348 80 100 1-351 80 100 2-349 80 100 1-84 80 100 2-84 80 100 1-352 80 100 2-350 80 100 1-86 80 100 2-86 80 100 1-92 80 100 2-92 80 100 1-90 80 100 2-90 80 100 1-353 80 100 2-351 80 100 2-352 80 80 1-355 80 100 2-353 80 100 1-356 80 100 2-354 80 100

TABLE 15c Pre-emergence action at 320 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 3-129 320 100 2-129 320 100 1-129 320 100 6-116 320 100 1-338 320 100 2-338 320 100 3-338 320 100 6-253 320 100 2-337 320 100 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 90 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

TABLE 16a Pre-emergence action at 20 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 2-337 20 90 3-337 20 90 2-123 20 80 1-26 20 100 2-26 20 100 6-26 20 100 1-208 20 100 2-208 20 90 6-159 20 90 1-130 20 100 2-130 20 100 1-131 20 100 2-131 20 90 6-118 20 90 1-149 20 100 2-149 20 90 5-59 20 100 5-58 20 90 5-117 20 100 5-253 20 80 5-75 20 100 5-74 20 90 5-123 20 100 5-122 20 100 1-82 20 100 1-87 20 100 2-87 20 100 1-88 20 100 2-88 20 100 1-209 20 100 1-25 20 90 2-25 20 100 1-27 20 100 2-27 20 100 1-173 20 100 2-173 20 100 1-273 20 100 2-273 20 100 3-273 20 90 6-212 20 100 4-212 20 80 4-212 20 80 1-44 20 90 2-44 20 100 1-45 20 100 2-45 20 90 6-32 20 90 1-46 20 90 2-46 20 100 6-33 20 80 1-30 20 100 2-30 20 100 1-31 20 100 2-31 20 100 1-28 20 100 2-28 20 100 1-29 20 100 2-29 20 90 1-304 20 100 2-304 20 90 6-231 20 80 1-305 20 100 2-305 20 100 1-306 20 100 2-306 20 100 1-177 20 100 2-177 20 100 1-178 20 100 2-178 20 100 6-141 20 90 1-179 20 100 2-179 20 100 1-132 20 100 2-132 20 80 1-135 20 90 2-135 20 100 6-254 20 90 1-134 20 90 2-134 20 80 1-133 20 90 1-277 20 100 2-277 20 90 1-278 20 100 2-278 20 100 1-279 20 100 2-279 20 90 2-195 20 90 2-225 20 100 1-197 20 100 2-227 20 90 1-227 20 100 2-197 20 100 6-165 20 90 6-166 20 80 2-196 20 90 6-45 20 90 2-57 20 100 2-58 20 100 2-56 20 100 1-57 20 100 1-207 20 100 2-207 20 90 2-271 20 100 6-210 20 100 2-32 20 100 1-34 20 100 2-34 20 100 6-255 20 100 2-33 20 100 2-42 20 100 6-256 20 90 1-146 20 100 1-141 20 90 1-37 20 80 1-72 20 90 2-72 20 100 1-73 20 90 2-73 20 90 1-74 20 100 2-74 20 100 1-144 20 90 1-138 20 100 2-138 20 100 1-137 20 100 1-136 20 100 1-180 20 100 2-180 20 100 1-183 20 100 2-183 20 90 1-182 20 100 2-182 20 100 6-145 20 90 1-181 20 100 6-144 20 90 1-228 20 100 2-228 20 100 1-230 20 90 2-230 20 100 2-286 20 100 1-287 20 100 2-287 20 100 2-288 20 100 1-210 20 100 2-210 20 100 1-212 20 100 2-213 20 80 1-288 20 100 1-289 20 100 2-289 20 100 6-228 20 90 1-291 20 100 2-291 20 100 2-292 20 100 1-271 20 100 2-47 20 100 6-34 20 100 1-339 20 100 2-339 20 100 6-258 20 100 1-49 20 90 2-49 20 100 1-229 20 100 1-340 20 100 2-340 20 100 1-47 20 100 1-33 20 100 1-32 20 100 2-154 20 100 6-259 20 100 1-155 20 100 2-155 20 100 6-260 20 100 6-261 20 80 1-165 20 100 1-156 20 100 2-156 20 100 6-262 20 100

TABLE 16b Pre-emergence action at 80 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 1-337 80 100 2-337 80 100 3-337 80 100 6-252 80 90 1-123 80 90 2-123 80 90 1-26 80 100 2-26 80 100 3-26 80 100 6-26 80 100 1-208 80 100 2-208 80 100 3-208 80 80 6-159 80 100 1-125 80 90 3-125 80 80 1-130 80 100 2-130 80 100 6-117 80 100 1-81 80 100 2-81 80 100 2-82 80 100 6-58 80 100 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 100 1-131 80 100 2-131 80 100 6-118 80 100 1-149 80 100 2-149 80 100 6-124 80 100 5-59 80 100 5-58 80 100 5-117 80 100 5-253 80 90 5-75 80 100 5-74 80 100 5-123 80 100 5-122 80 100 1-82 80 100 1-87 80 100 2-87 80 100 1-88 80 100 2-88 80 100 6-75 80 80 1-209 80 100 1-4 80 100 1-25 80 100 2-25 80 100 3-27 80 100 1-27 80 100 2-27 80 100 1-173 80 100 2-173 80 100 1-273 80 100 2-273 80 100 3-273 80 100 6-212 80 100 4-212 80 90 4-212 80 90 1-44 80 100 2-44 80 100 1-45 80 100 2-45 80 100 6-32 80 100 1-46 80 100 2-46 80 100 6-33 80 100 1-30 80 100 2-30 80 100 1-31 80 100 2-31 80 100 1-28 80 100 2-28 80 100 1-29 80 100 2-29 80 100 1-304 80 100 2-304 80 100 6-231 80 90 1-305 80 100 2-305 80 100 1-306 80 100 2-306 80 100 6-233 80 90 1-177 80 100 2-177 80 100 1-178 80 100 2-178 80 100 6-141 80 100 1-179 80 100 2-179 80 100 1-132 80 100 2-132 80 100 1-135 80 100 2-135 80 100 6-254 80 100 1-134 80 100 2-134 80 100 1-133 80 100 2-133 80 90 6-120 80 90 1-277 80 100 2-277 80 100 1-278 80 100 2-278 80 100 1-279 80 100 2-279 80 100 2-195 80 100 2-225 80 100 1-197 80 100 2-227 80 100 1-227 80 100 2-197 80 100 1-225 80 90 1-226 80 90 6-165 80 100 6-166 80 100 2-196 80 100 1-56 80 80 6-45 80 100 2-57 80 100 6-43 80 100 1-58 80 80 2-58 80 100 2-56 80 100 1-57 80 100 1-207 80 100 2-207 80 100 2-271 80 100 6-210 80 100 2-32 80 100 1-34 80 100 2-34 80 100 6-255 80 100 2-33 80 100 2-42 80 100 6-256 80 100 2-146 80 100 1-143 80 80 1-146 80 100 1-141 80 100 1-37 80 100 2-37 80 100 1-72 80 100 2-72 80 100 1-73 80 100 2-73 80 100 6-50 80 100 1-74 80 100 2-74 80 100 6-51 80 100 1-144 80 90 2-144 80 100 1-138 80 100 2-138 80 100 2-141 80 90 1-137 80 100 1-136 80 100 1-180 80 100 2-180 80 100 6-143 80 100 1-183 80 100 2-183 80 100 6-257 80 100 1-182 80 100 2-182 80 100 6-145 80 100 1-181 80 100 2-181 80 100 6-144 80 100 2-36 80 90 1-228 80 100 2-228 80 100 6-167 80 90 1-230 80 100 2-230 80 100 6-169 80 90 2-286 80 100 1-287 80 100 2-287 80 100 2-288 80 100 1-210 80 100 2-210 80 100 1-212 80 100 2-212 80 100 2-213 80 100 1-288 80 100 1-289 80 100 2-289 80 100 6-228 80 100 1-291 80 100 2-291 80 100 6-230 80 80 2-292 80 100 1-271 80 100 2-47 80 100 6-34 80 100 1-339 80 100 2-339 80 100 6-258 80 100 1-49 80 100 2-49 80 100 1-41 80 100 1-229 80 100 2-229 80 100 1-340 80 100 2-340 80 100 1-47 80 100 1-33 80 100 1-32 80 100 2-154 80 100 6-259 80 100 1-155 80 100 2-155 80 100 6-260 80 100 1-164 80 80 2-164 80 100 6-261 80 100 1-165 80 100 1-166 80 90 1-156 80 100 2-156 80 100 6-262 80 100

TABLE 16c Pre-emergence action at 320 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 2-337 320 100 6-252 320 90 6-117 320 100 1-81 320 100 2-81 320 100 2-82 320 100 6-58 320 100 1-147 320 100 2-147 320 100 1-148 320 100 2-148 320 100

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate equivalent to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Numerous compounds of the invention showed very good action against a multitude of important harmful plants. The tables below illustrate, in an illustrative manner, the post-emergence herbicidal action of the compounds of the invention, the herbicidal activity being stated in percent.

TABLE 17a Post-emergence action at 5 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 3-129 5 100 2-129 5 100 1-129 5 100 6-116 5 90 1-338 5 90 2-338 5 100 3-338 5 90 6-253 5 100 3-337 5 80 1-26 5 90 2-26 5 100 3-26 5 80 6-26 5 90 1-208 5 80 2-208 5 90 3-208 5 90 6-159 5 90 1-130 5 90 2-130 5 90 1-131 5 90 6-118 5 80 1-149 5 80 2-149 5 80 6-124 5 80 5-59 5 90 5-58 5 90 5-117 5 80 5-253 5 90 5-75 5 90 5-74 5 90 5-123 5 90 5-122 5 80 1-82 5 90 1-87 5 90 2-87 5 90 1-88 5 90 2-88 5 90 1-209 5 90 1-4 5 90 1-25 5 100 2-25 5 100 1-27 5 100 2-27 5 100 2-173 5 90 1-273 5 90 2-273 5 90 3-273 5 80 6-212 5 80 1-44 5 90 2-44 5 80 1-45 5 80 2-45 5 80 6-32 5 80 1-46 5 90 2-46 5 80 1-30 5 80 2-30 5 80 1-31 5 80 1-28 5 80 2-28 5 80 1-304 5 90 2-304 5 90 1-305 5 90 2-305 5 80 1-306 5 80 1-177 5 90 2-177 5 80 1-178 5 80 2-178 5 90 1-277 5 90 2-277 5 80 1-278 5 80 2-278 5 80 1-279 5 80 2-195 5 100 2-225 5 100 2-227 5 100 1-227 5 100 1-225 5 80 1-226 5 90 1-56 5 80 6-45 5 80 2-57 5 90 1-58 5 90 2-58 5 100 2-56 5 100 1-57 5 90 1-207 5 80 2-271 5 100 2-32 5 90 1-34 5 90 2-34 5 90 6-255 5 90 2-33 5 90 2-42 5 80 6-256 5 80 1-72 5 80 2-72 5 80 1-73 5 80 2-73 5 80 1-74 5 80 2-74 5 80 2-286 5 90 1-287 5 90 2-287 5 80 2-288 5 80 1-210 5 80 2-210 5 80 1-288 5 80 1-289 5 80 1-291 5 80 2-291 5 80 1-271 5 80 2-47 5 90 2-47 5 80 6-34 5 80 2-339 5 80 6-258 5 80 1-49 5 90 2-49 5 90 1-41 5 80 1-32 5 90 2-154 5 80 1-155 5 80 2-155 5 80 1-164 5 80 1-165 5 90 1-166 5 90 1-156 5 90 6-262 5 80 2-211 5 80 2-272 5 90 2-276 5 80 1-276 5 80 1-272 5 80 6-211 5 80 1-83 5 90 2-83 5 90 1-89 5 90 2-89 5 90 1-342 5 90 1-343 5 90 2-342 5 80 1-345 5 80 2-344 5 90 1-346 5 80 2-345 5 90 1-347 5 80 2-346 5 90 1-184 5 80 2-184 5 90 1-185 5 80 2-185 5 90 1-186 5 90 2-186 5 80 1-349 5 80 2-348 5 90 1-86 5 100 2-86 5 80 1-92 5 90 2-92 5 80 1-90 5 80 1-354 5 90 1-355 5 80 2-353 5 90 2-354 5 90

TABLE 17b Post-emergence action at 20 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 90 2-338 20 100 3-338 20 90 6-253 20 100 1-337 20 80 2-337 20 100 3-337 20 80 6-252 20 80 1-123 20 80 1-26 20 100 2-26 20 100 3-26 20 90 6-26 20 90 1-208 20 90 2-208 20 90 3-208 20 90 6-159 20 100 3-125 20 80 1-130 20 90 2-130 20 90 6-117 20 80 1-81 20 80 2-81 20 90 2-82 20 90 6-58 20 80 1-147 20 90 2-147 20 90 1-148 20 90 2-148 20 90 1-131 20 90 2-131 20 90 6-118 20 90 1-149 20 100 2-149 20 100 6-124 20 80 5-59 20 90 5-58 20 90 5-117 20 90 5-253 20 90 5-75 20 90 5-74 20 90 5-123 20 90 5-122 20 90 1-82 20 90 1-87 20 90 2-87 20 90 1-88 20 90 2-88 20 90 1-209 20 100 1-4 20 90 1-25 20 100 2-25 20 100 3-27 20 100 1-27 20 100 2-27 20 100 1-173 20 90 2-173 20 100 1-273 20 90 2-273 20 90 3-273 20 90 6-212 20 90 4-212 20 80 1-44 20 100 2-44 20 90 1-45 20 90 2-45 20 80 6-32 20 80 1-46 20 90 2-46 20 80 6-33 20 80 1-30 20 80 2-30 20 80 1-31 20 80 2-31 20 80 1-28 20 80 2-28 20 80 1-29 20 80 2-29 20 80 1-304 20 90 2-304 20 90 1-305 20 90 2-305 20 90 1-306 20 80 2-306 20 80 1-177 20 90 2-177 20 90 1-178 20 80 2-178 20 90 6-141 20 80 1-179 20 80 2-179 20 90 1-132 20 80 2-132 20 80 1-135 20 80 2-135 20 80 6-254 20 80 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 90 1-279 20 90 2-279 20 80 2-195 20 100 2-225 20 100 1-197 20 100 2-227 20 100 1-227 20 100 2-197 20 80 1-225 20 80 1-226 20 90 2-226 20 90 6-165 20 90 6-166 20 80 2-196 20 100 1-56 20 100 6-45 20 90 6-44 20 80 2-57 20 100 1-58 20 90 2-58 20 100 2-56 20 100 1-57 20 90 1-207 20 90 2-207 20 90 2-271 20 100 6-210 20 90 2-32 20 90 1-34 20 100 2-34 20 90 6-255 20 90 2-33 20 90 2-42 20 90 6-256 20 90 2-146 20 80 1-146 20 80 2-143 20 80 1-72 20 90 2-72 20 80 6-49 20 80 1-73 20 80 2-73 20 80 6-50 20 80 1-74 20 80 2-74 20 80 2-230 20 80 2-286 20 90 1-287 20 100 2-287 20 80 2-288 20 80 1-210 20 90 2-210 20 80 1-212 20 80 2-213 20 80 1-288 20 80 1-289 20 80 2-289 20 80 1-291 20 90 2-291 20 80 2-292 20 80 1-271 20 90 2-47 20 90 2-47 20 90 6-34 20 80 2-339 20 80 6-258 20 90 1-49 20 90 2-49 20 90 1-41 20 80 2-229 20 80 1-340 20 80 6-267 20 80 1-47 20 80 1-33 20 90 1-32 20 90 2-154 20 90 6-259 20 80 1-155 20 90 2-155 20 80 6-260 20 90 1-164 20 80 6-261 20 80 1-165 20 90 1-166 20 90 1-156 20 90 2-156 20 90 6-262 20 90 1-159 20 80 2-160 20 90 2-161 20 80 2-211 20 80 2-272 20 90 2-276 20 80 1-276 20 80 1-211 20 80 1-274 20 80 1-272 20 90 6-211 20 90 1-341 20 80 1-292 20 80 2-341 20 80 1-158 20 80 1-83 20 90 2-83 20 90 6-60 20 90 1-89 20 90 2-89 20 90 6-161 20 90 1-342 20 90 1-343 20 90 2-342 20 90 1-344 20 90 2-343 20 80 1-345 20 90 2-344 20 90 1-346 20 100 2-345 20 90 1-347 20 90 2-346 20 90 1-195 20 80 1-184 20 80 2-184 20 90 1-185 20 90 2-185 20 100 1-186 20 90 2-186 20 90 1-349 20 90 2-348 20 90 1-351 20 80 2-349 20 80 2-84 20 90 1-352 20 100 2-350 20 80 1-86 20 100 2-86 20 100 1-92 20 100 2-92 20 90 1-90 20 90 2-90 20 90 1-353 20 80 2-351 20 80 1-354 20 100 2-352 20 80 1-355 20 100 2-353 20 100 1-356 20 100 2-354 20 90

TABLE 17c Post-emergence action at 80 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 100 6-253 80 100 2-337 80 100 6-252 80 100 6-117 80 80 1-81 80 90 2-81 80 90 2-82 80 90 6-58 80 80 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90

TABLE 18a Post-emergence action at 5 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY 2-129 5 100 1-129 5 90 2-27 5 80 1-273 5 80 2-177 5 80 1-178 5 90 2-178 5 80 1-179 5 90 1-132 5 80 2-195 5 80 1-226 5 80 2-32 5 90 2-33 5 90 2-42 5 90 1-136 5 80 1-182 5 90 2-182 5 80 1-181 5 80 1-210 5 80 1-212 5 80 2-291 5 80 1-271 5 80 2-47 5 80 1-47 5 80 1-32 5 80 1-165 5 90 1-166 5 80 1-342 5 90 1-343 5 90 2-342 5 90 2-343 5 80 1-345 5 80 2-344 5 80 1-346 5 80 2-345 5 80 1-195 5 90 1-184 5 80 2-184 5 80 1-186 5 80 2-348 5 80 1-351 5 90 2-352 5 80

TABLE 18b Post-emergence action at 20 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY 3-129 20 80 2-129 20 100 1-129 20 100 6-116 20 80 2-338 20 80 1-26 20 90 2-26 20 80 3-26 20 80 1-208 20 80 2-208 20 80 6-159 20 80 1-130 20 80 2-130 20 80 6-117 20 80 1-81 20 80 2-81 20 80 1-147 20 80 2-147 20 80 1-148 20 80 2-148 20 80 1-131 20 90 2-131 20 80 6-118 20 80 1-149 20 80 2-149 20 80 6-124 20 90 5-59 20 80 5-58 20 80 5-117 20 80 5-75 20 80 5-123 20 80 5-122 20 80 1-82 20 90 1-87 20 80 2-87 20 80 1-88 20 80 2-88 20 80 1-209 20 80 1-4 20 80 1-25 20 100 2-25 20 90 1-27 20 100 2-27 20 90 1-173 20 80 2-173 20 100 1-273 20 100 2-273 20 80 6-212 20 80 1-46 20 90 2-46 20 80 1-30 20 80 2-31 20 80 1-177 20 90 2-177 20 100 1-178 20 100 2-178 20 90 6-141 20 90 1-179 20 90 2-179 20 90 1-132 20 90 1-135 20 90 2-134 20 80 1-133 20 90 2-133 20 80 2-278 20 80 2-195 20 100 2-197 20 90 1-225 20 90 1-226 20 100 2-226 20 90 6-165 20 80 2-196 20 90 2-57 20 90 2-58 20 80 2-56 20 80 1-57 20 80 1-207 20 90 2-207 20 90 2-271 20 100 2-32 20 100 1-34 20 90 2-34 20 100 6-255 20 90 2-33 20 100 2-42 20 100 2-142 20 80 1-142 20 90 2-74 20 80 1-138 20 90 1-137 20 90 1-136 20 90 2-180 20 90 1-183 20 90 2-183 20 80 1-182 20 100 2-182 20 100 6-145 20 80 1-181 20 100 2-181 20 90 2-36 20 90 1-228 20 90 2-228 20 80 1-230 20 90 2-230 20 90 2-287 20 90 2-288 20 90 1-210 20 100 2-210 20 90 1-212 20 90 1-288 20 90 2-289 20 90 1-291 20 90 2-291 20 80 2-292 20 80 1-271 20 90 2-47 20 90 2-47 20 90 1-339 20 80 2-339 20 80 6-258 20 80 2-49 20 80 1-229 20 80 1-340 20 80 1-47 20 90 1-33 20 90 1-32 20 90 2-154 20 80 1-155 20 90 2-155 20 90 1-165 20 100 1-166 20 90 1-156 20 80 2-156 20 90 1-160 20 80 2-160 20 80 2-211 20 80 2-272 20 90 2-276 20 80 1-276 20 80 1-274 20 80 1-272 20 90 1-341 20 80 1-292 20 80 1-83 20 100 2-83 20 100 1-89 20 90 2-89 20 90 6-161 20 90 1-342 20 100 1-343 20 100 2-342 20 90 1-344 20 100 2-343 20 100 1-345 20 90 2-344 20 90 1-346 20 90 2-345 20 80 1-347 20 80 2-346 20 80 1-195 20 100 1-184 20 80 2-184 20 100 1-185 20 90 2-185 20 90 1-186 20 90 2-186 20 80 1-349 20 80 2-348 20 90 1-351 20 90 2-349 20 80 1-84 20 100 2-84 20 90 1-352 20 80 2-350 20 80 1-86 20 100 2-86 20 80 1-92 20 90 2-92 20 80 1-90 20 80 1-353 20 80 2-351 20 80 1-354 20 80 2-352 20 90 1-355 20 80 1-356 20 80 2-354 20 80

TABLE 18c Post-emergence action at 80 g/ha against ALOMY in % Dosage Example number [g/ha] ALOMY 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 100 6-253 80 80 2-337 80 90 6-117 80 90 1-81 80 90 2-81 80 90 2-82 80 90 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90

TABLE 19a Post-emergence action at 5 g/ha against AMARE in % Example Dosage number [g/ha] ALOMY 3-129 5 90 2-129 5 100 1-129 5 100 6-116 5 100 1-338 5 90 2-338 5 80 3-338 5 90 2-337 5 80 3-337 5 90 2-123 5 80 1-26 5 90 2-26 5 100 3-26 5 90 6-26 5 100 1-208 5 100 2-208 5 90 3-208 5 80 6-159 5 90 1-130 5 90 2-130 5 90 1-131 5 100 2-131 5 100 6-118 5 100 1-149 5 90 2-149 5 100 6-124 5 100 5-59 5 90 5-58 5 90 5-117 5 100 5-253 5 80 5-75 5 90 5-74 5 90 5-123 5 90 5-122 5 90 1-82 5 90 1-87 5 90 2-87 5 90 1-88 5 90 2-88 5 90 1-209 5 90 1-4 5 80 1-25 5 100 1-27 5 100 2-27 5 100 1-173 5 100 2-173 5 100 1-273 5 90 6-212 5 80 1-44 5 100 2-44 5 100 1-45 5 90 2-45 5 100 6-32 5 80 1-46 5 100 2-46 5 100 6-33 5 90 1-304 5 90 2-304 5 90 6-231 5 80 1-305 5 90 2-305 5 100 1-306 5 100 2-306 5 90 1-177 5 90 2-177 5 100 1-178 5 90 2-178 5 100 6-141 5 90 1-179 5 100 2-179 5 100 1-132 5 100 2-132 5 80 1-135 5 90 2-135 5 90 6-254 5 80 1-134 5 90 2-134 5 80 1-133 5 90 2-133 5 80 6-120 5 80 1-277 5 100 2-277 5 90 1-278 5 90 2-278 5 90 1-279 5 90 2-195 5 100 2-225 5 100 1-197 5 100 2-227 5 100 1-227 5 100 2-197 5 80 1-225 5 90 1-226 5 90 2-226 5 90 1-56 5 100 2-57 5 100 1-58 5 100 2-58 5 100 2-56 5 100 1-57 5 100 1-207 5 100 2-207 5 100 2-271 5 100 6-210 5 100 2-32 5 100 1-34 5 100 2-34 5 100 6-255 5 100 2-33 5 100 2-42 5 100 6-256 5 80 2-146 5 80 1-141 5 90 1-144 5 80 1-138 5 80 2-138 5 90 2-141 5 80 1-137 5 90 1-136 5 90 1-181 5 100 1-228 5 90 6-167 5 80 2-286 5 90 2-287 5 90 2-288 5 90 1-212 5 90 1-288 5 90 1-289 5 90 2-289 5 90 1-291 5 80 6-230 5 90 2-292 5 80 1-271 5 90 2-47 5 90 2-47 5 100 6-34 5 90 1-339 5 80 2-339 5 80 6-258 5 90 1-49 5 90 2-49 5 90 1-41 5 80 1-229 5 90 2-229 5 80 1-340 5 90 6-267 5 90 2-340 5 90 1-47 5 90 1-33 5 80 1-32 5 90 2-154 5 90 6-259 5 80 1-155 5 90 2-155 5 90 1-164 5 90 2-164 5 80 6-261 5 80 1-165 5 90 1-166 5 80 1-156 5 80 2-156 5 90 1-159 5 90 2-159 5 90 1-162 5 90 2-162 5 80 1-160 5 90 2-160 5 90 2-161 5 90 6-266 5 80 2-211 5 90 2-272 5 90 1-161 5 80 2-276 5 80 1-276 5 100 1-211 5 90 1-274 5 100 6-168 5 80 1-272 5 90 6-211 5 80 1-341 5 80 1-292 5 80 2-341 5 90 1-158 5 80 1-83 5 100 2-83 5 100 6-60 5 80 1-89 5 100 2-89 5 100 6-76 5 100 6-161 5 100 6-268 5 90 1-342 5 100 1-343 5 100 2-342 5 100 1-344 5 100 2-343 5 90 1-345 5 100 2-344 5 100 1-346 5 100 2-345 5 90 1-347 5 100 2-346 5 100 1-195 5 100 1-184 5 100 2-184 5 100 1-185 5 100 2-185 5 100 1-186 5 90 2-186 5 100 1-349 5 100 1-350 5 90 2-348 5 90 1-351 5 100 2-349 5 90 1-84 5 100 2-84 5 100 1-352 5 100 2-350 5 100 1-86 5 100 2-86 5 100 1-92 5 100 2-92 5 100 1-90 5 100 2-90 5 100 1-353 5 100 2-351 5 100 1-354 5 90 2-352 5 100 1-355 5 100 2-353 5 100 1-356 5 100 2-354 5 100

TABLE 19b Post-emergence action at 20 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 90 2-338 20 100 3-338 20 90 2-337 20 100 3-337 20 100 1-123 20 80 2-123 20 80 1-26 20 100 2-26 20 100 3-26 20 90 6-26 20 100 1-208 20 100 2-208 20 100 3-208 20 90 6-159 20 100 1-125 20 80 2-125 20 80 3-125 20 90 1-130 20 90 2-130 20 100 1-81 20 90 2-81 20 90 2-82 20 90 1-147 20 90 2-147 20 90 1-148 20 90 2-148 20 90 1-131 20 100 2-131 20 100 6-118 20 100 1-149 20 100 2-149 20 100 6-124 20 100 5-59 20 90 5-58 20 90 5-117 20 100 5-253 20 80 5-75 20 90 5-74 20 100 5-123 20 90 5-122 20 90 1-82 20 90 1-87 20 100 2-87 20 90 1-88 20 90 2-88 20 90 1-209 20 100 1-4 20 90 1-25 20 100 1-27 20 100 2-27 20 100 1-173 20 100 2-173 20 100 1-273 20 100 2-273 20 90 6-212 20 90 4-212 20 80 1-44 20 100 2-44 20 100 1-45 20 90 2-45 20 100 6-32 20 100 1-46 20 100 2-46 20 100 6-33 20 90 2-31 20 80 1-304 20 90 2-304 20 100 6-231 20 90 1-305 20 90 2-305 20 100 1-306 20 100 2-306 20 90 1-177 20 100 2-177 20 100 1-178 20 100 2-178 20 100 6-141 20 100 1-179 20 100 2-179 20 100 1-132 20 100 2-132 20 90 1-135 20 90 2-135 20 90 6-254 20 100 1-134 20 90 2-134 20 100 1-133 20 100 2-133 20 90 6-120 20 90 1-277 20 100 2-277 20 90 1-278 20 90 2-278 20 100 1-279 20 100 2-279 20 100 2-195 20 100 2-225 20 100 1-197 20 100 2-227 20 100 1-227 20 100 2-197 20 90 1-225 20 100 1-226 20 100 2-226 20 100 6-165 20 80 6-166 20 90 1-56 20 100 6-45 20 80 6-44 20 90 2-57 20 100 1-58 20 100 2-58 20 100 2-56 20 100 1-57 20 100 1-207 20 100 2-207 20 100 2-271 20 100 6-210 20 100 2-32 20 100 1-34 20 100 2-34 20 100 6-255 20 100 2-33 20 100 2-42 20 100 6-256 20 90 2-146 20 80 2-142 20 100 5-255 20 90 1-142 20 90 5-254 20 80 1-140 20 80 1-146 20 100 1-141 20 100 1-144 20 90 1-138 20 90 2-138 20 90 2-141 20 80 1-137 20 90 1-136 20 90 1-181 20 100 1-36 20 100 2-36 20 90 1-228 20 90 2-228 20 90 6-167 20 100 1-230 20 100 2-230 20 100 6-169 20 90 2-286 20 100 2-287 20 100 2-288 20 100 2-210 20 100 1-212 20 100 1-288 20 100 1-289 20 90 2-289 20 100 6-228 20 90 1-291 20 90 2-291 20 90 6-230 20 90 2-292 20 90 1-271 20 90 2-47 20 90 2-47 20 100 6-34 20 100 1-339 20 90 2-339 20 90 6-258 20 90 1-49 20 90 2-49 20 100 1-41 20 90 1-229 20 90 2-229 20 90 1-340 20 90 6-267 20 90 2-340 20 100 1-47 20 90 1-33 20 100 1-32 20 90 2-154 20 90 6-259 20 100 1-155 20 90 2-155 20 90 6-260 20 80 1-164 20 90 2-164 20 90 6-261 20 90 1-165 20 90 1-166 20 90 1-156 20 90 2-156 20 90 6-262 20 90 2-157 20 90 1-159 20 100 2-159 20 100 1-162 20 90 2-162 20 100 6-264 20 80 1-160 20 100 2-160 20 100 2-161 20 100 6-266 20 100 2-211 20 90 2-272 20 100 1-161 20 90 2-276 20 90 1-276 20 100 1-211 20 90 1-274 20 100 6-168 20 100 1-272 20 100 6-211 20 90 1-341 20 100 1-292 20 100 2-341 20 100 1-158 20 90 1-83 20 100 2-83 20 100 6-60 20 100 1-89 20 100 2-89 20 100 6-76 20 100 6-161 20 100 6-268 20 100 1-342 20 100 1-343 20 100 2-342 20 100 1-344 20 100 2-343 20 100 1-345 20 100 2-344 20 100 1-346 20 100 2-345 20 100 1-347 20 100 2-346 20 100 1-195 20 100 1-184 20 100 2-184 20 100 1-185 20 100 2-185 20 100 1-186 20 100 2-186 20 100 1-349 20 100 1-350 20 100 2-348 20 100 1-351 20 100 2-349 20 100 1-84 20 100 2-84 20 100 1-352 20 100 2-350 20 100 1-86 20 100 2-86 20 100 1-92 20 100 2-92 20 100 1-90 20 100 2-90 20 100 1-353 20 100 2-351 20 100 1-354 20 100 2-352 20 100 1-355 20 100 2-353 20 100 1-356 20 100 2-354 20 100

TABLE 19c Post-emergence action at 80 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 100 6-253 80 100 2-337 80 100 6-117 80 80 1-81 80 90 2-81 80 90 2-82 80 90 6-58 80 90 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90

TABLE 20a Post-emergence action at 5 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 2-129 5 100 6-116 5 100 2-208 5 80 2-131 5 80 5-117 5 80 2-27 5 90 1-173 5 90 1-28 5 80 2-28 5 80 1-29 5 80 1-132 5 80 2-32 5 90 2-34 5 80

TABLE 20b Post-emergence action at 20 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 80 2-338 20 80 3-337 20 80 2-26 20 80 1-208 20 90 2-208 20 90 3-208 20 80 1-130 20 80 2-130 20 90 2-81 20 90 2-82 20 90 6-58 20 80 1-147 20 90 2-147 20 90 1-148 20 100 2-148 20 90 1-131 20 80 2-131 20 80 1-149 20 100 5-117 20 90 5-75 20 80 5-74 20 80 5-123 20 80 5-122 20 80 1-82 20 90 1-87 20 80 2-87 20 80 1-88 20 80 2-88 20 80 1-4 20 80 2-25 20 100 3-27 20 90 1-27 20 100 2-27 20 100 1-173 20 100 2-173 20 100 1-273 20 90 3-273 20 80 1-44 20 80 2-44 20 80 1-46 20 80 1-30 20 80 1-31 20 90 2-31 20 80 1-28 20 80 2-28 20 90 1-29 20 90 2-29 20 80 1-178 20 80 2-178 20 80 1-179 20 90 1-132 20 90 2-135 20 80 1-277 20 80 2-195 20 80 1-227 20 80 1-225 20 80 1-226 20 80 2-226 20 80 2-57 20 80 1-58 20 90 2-58 20 80 2-271 20 80 2-32 20 100 2-34 20 80 2-33 20 100 1-137 20 80 2-182 20 80 1-181 20 90 2-230 20 80 2-288 20 80 1-212 20 80 1-291 20 80 2-291 20 90 2-292 20 80 1-271 20 80 2-47 20 80 1-49 20 80 1-165 20 90 2-272 20 80 2-341 20 90 2-83 20 90 2-89 20 80 1-344 20 80 2-345 20 80 1-349 20 80 1-351 20 80 2-349 20 90 1-84 20 80 2-84 20 100 1-352 20 80 2-350 20 90 1-86 20 100 2-86 20 80 1-92 20 90 2-92 20 80 2-90 20 80 1-353 20 80 2-351 20 80

TABLE 20c Post-emergence action at 80 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 100 6-253 80 80 2-337 80 90 6-117 80 90 1-81 80 90 2-81 80 100 2-82 80 90 6-58 80 90 1-147 80 90 2-147 80 100 1-148 80 100 2-148 80 90

TABLE 21a Post-emergence action at 20 g/ha against CYPES in % Example Dosage number [g/ha] CYPES 1-338 20 80

TABLE 21b Post-emergence action at 80 g/ha against CYPES in % Example Dosage number [g/ha] CYPES 2-129 80 90 1-129 80 80 1-338 80 90 6-253 80 80

TABLE 22a Post-emergence action at 5 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 1-129 5 100 2-26 5 80 6-26 5 80 6-159 5 80 1-130 5 80 5-59 5 80 5-58 5 80 5-117 5 80 5-75 5 80 5-74 5 80 5-123 5 90 5-122 5 90 1-82 5 80 1-87 5 80 2-87 5 80 1-88 5 80 2-88 5 80 2-27 5 80 2-173 5 80 1-273 5 80 2-273 5 80 3-273 5 80 6-212 5 90 1-45 5 80 1-46 5 80 2-30 5 80 1-31 5 80 2-31 5 80 1-28 5 80 2-28 5 80 2-305 5 90 1-306 5 90 2-306 5 90 1-135 5 80 2-135 5 80 1-278 5 90 1-279 5 80 1-225 5 90 1-226 5 100 6-165 5 90 6-166 5 80 1-56 5 80 2-57 5 100 1-58 5 90 2-58 5 90 1-57 5 80 2-32 5 80 1-34 5 90 2-34 5 90 6-255 5 90 2-33 5 90 2-42 5 90 6-256 5 90 1-37 5 80 2-72 5 80 1-73 5 80 2-73 5 80 1-74 5 80 2-74 5 80 1-138 5 80 2-138 5 80 1-137 5 90 1-136 5 80 6-257 5 80 2-182 5 90 1-181 5 80 2-228 5 80 1-230 5 80 6-169 5 80 2-287 5 80 2-288 5 80 1-212 5 80 2-213 5 80 1-288 5 80 2-289 5 80 1-291 5 80 2-291 5 80 2-292 5 80 1-271 5 80 2-47 5 80 2-47 5 80 6-34 5 80 1-339 5 90 6-258 5 80 1-49 5 80 1-229 5 90 1-47 5 90 1-33 5 80 6-259 5 80 1-155 5 90 6-260 5 90 1-164 5 80 1-156 5 80 2-156 5 90 2-272 5 80 1-211 5 80 1-274 5 80 6-168 5 80 1-272 5 80 1-341 5 80 1-292 5 80 2-341 5 80 6-161 5 90 1-343 5 80 2-344 5 80 1-346 5 80 2-346 5 80 1-185 5 90 2-84 5 100 1-352 5 100 1-86 5 80 2-86 5 100 1-92 5 100 2-92 5 80 1-353 5 100 2-351 5 100

TABLE 22b Post-emergence action at 20 G/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 90 2-338 20 80 1-26 20 80 2-26 20 80 6-26 20 90 2-208 20 80 6-159 20 90 1-130 20 80 2-130 20 80 6-117 20 80 1-81 20 80 2-81 20 90 2-82 20 80 6-58 20 90 1-147 20 90 2-147 20 90 1-148 20 80 2-148 20 80 1-131 20 90 2-131 20 80 6-118 20 90 1-149 20 80 2-149 20 80 6-124 20 80 5-59 20 90 5-58 20 90 5-117 20 80 5-253 20 80 5-75 20 80 5-74 20 80 5-123 20 90 5-122 20 90 1-82 20 90 1-87 20 80 2-87 20 80 1-88 20 90 2-88 20 80 1-209 20 90 1-4 20 100 1-25 20 100 2-25 20 80 1-27 20 80 2-27 20 100 1-173 20 80 2-173 20 90 1-273 20 90 2-273 20 90 3-273 20 80 6-212 20 90 1-44 20 80 2-44 20 80 1-45 20 80 2-45 20 80 1-46 20 80 2-46 20 80 6-33 20 80 1-30 20 80 2-30 20 80 1-31 20 80 2-31 20 90 1-28 20 90 2-28 20 80 1-29 20 80 2-29 20 80 1-304 20 90 2-304 20 80 1-305 20 90 2-305 20 90 1-306 20 90 2-306 20 90 6-233 20 80 1-177 20 90 1-178 20 90 2-178 20 90 6-141 20 80 1-179 20 90 2-179 20 80 1-132 20 90 2-132 20 90 1-135 20 100 2-135 20 90 6-254 20 90 1-134 20 90 2-134 20 90 2-133 20 80 6-120 20 90 1-277 20 90 2-277 20 100 1-278 20 90 2-278 20 90 1-279 20 90 2-279 20 90 2-225 20 100 1-197 20 90 2-227 20 80 2-197 20 90 1-225 20 100 1-226 20 100 2-226 20 90 6-165 20 100 6-166 20 90 2-196 20 80 1-56 20 90 6-45 20 90 6-44 20 90 2-57 20 100 1-58 20 90 2-58 20 100 2-56 20 100 1-57 20 100 1-207 20 80 6-210 20 80 2-32 20 90 1-34 20 90 2-34 20 100 6-255 20 100 2-33 20 100 2-42 20 100 6-256 20 90 1-146 20 80 1-37 20 80 2-37 20 80 1-72 20 80 2-72 20 80 1-73 20 80 2-73 20 80 6-50 20 80 1-74 20 80 2-74 20 80 6-51 20 80 1-138 20 90 2-138 20 90 2-141 20 80 1-137 20 90 1-136 20 90 2-180 20 90 1-183 20 100 2-183 20 90 6-257 20 90 1-182 20 80 2-182 20 90 1-181 20 80 2-181 20 90 6-144 20 80 1-228 20 80 2-228 20 90 6-167 20 80 1-230 20 80 6-169 20 90 2-286 20 100 1-287 20 100 2-287 20 80 2-288 20 80 1-210 20 80 2-210 20 90 1-212 20 80 2-212 20 80 2-213 20 80 1-288 20 80 1-289 20 80 2-289 20 90 1-291 20 80 2-291 20 80 2-292 20 80 1-271 20 80 2-47 20 90 2-47 20 80 6-34 20 90 1-339 20 90 2-339 20 90 6-258 20 90 1-49 20 90 2-49 20 90 1-41 20 90 1-229 20 90 2-229 20 90 1-340 20 90 6-267 20 90 2-340 20 90 1-47 20 90 1-33 20 90 1-32 20 90 2-154 20 90 6-259 20 90 1-155 20 90 6-260 20 90 1-164 20 90 2-164 20 80 6-261 20 90 1-165 20 90 1-166 20 90 1-156 20 90 2-156 20 90 6-262 20 80 1-159 20 90 1-162 20 80 2-211 20 80 2-272 20 90 2-276 20 90 1-276 20 80 1-211 20 90 1-274 20 90 6-168 20 80 1-272 20 90 6-211 20 90 1-341 20 90 1-292 20 80 2-341 20 90 1-83 20 90 2-83 20 90 6-60 20 90 2-89 20 90 6-76 20 80 6-161 20 90 1-342 20 80 1-343 20 90 1-345 20 90 2-344 20 90 1-346 20 90 2-345 20 80 1-347 20 90 2-346 20 90 1-195 20 80 1-184 20 100 2-184 20 100 1-185 20 100 2-185 20 100 1-186 20 90 1-350 20 80 2-348 20 80 1-351 20 100 1-84 20 100 2-84 20 100 1-352 20 100 2-350 20 100 1-86 20 100 2-86 20 100 1-92 20 100 2-92 20 100 1-90 20 100 2-90 20 100 1-353 20 100 2-351 20 100 2-352 20 90 1-355 20 90

TABLE 22c Post-emergence action at 80 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 100 3-338 80 80 6-253 80 90 2-337 80 90 6-117 80 80 1-81 80 90 2-81 80 90 2-82 80 80 6-58 80 90 1-147 80 90 2-147 80 90 1-148 80 80 2-148 80 90

TABLE 23a Post-emergence action at 5 g/ha against HORMU in % Example Dosage number [g/ha] HORMU 2-129 5 80 1-129 5 90 1-273 5 80

TABLE 23b Post-emergence action at 20 g/ha against HORMU in % Example Dosage number [g/ha] HORMU 3-129 20 90 2-129 20 90 1-129 20 100 6-116 20 90 1-338 20 80 2-26 20 80 6-117 20 80 2-82 20 80 1-147 20 80 2-147 20 80 2-148 20 80 1-131 20 80 2-131 20 100 5-59 20 80 5-117 20 80 5-122 20 80 1-82 20 90 1-87 20 80 2-87 20 80 2-88 20 80 1-25 20 100 2-25 20 80 1-27 20 80 2-27 20 90 1-173 20 90 2-173 20 100 1-273 20 90 2-46 20 80

TABLE 23c Post-emergence action at 80 g/ha against HORMU in % Example Dosage number [g/ha] HORMU 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 100 3-338 80 100 6-253 80 90 6-117 80 90 1-81 80 80 2-81 80 80 2-82 80 90 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90

TABLE 24a Post-emergence action at 5 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI 1-129 5 80

TABLE 24b Post-emergence action at 20 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI 2-129 20 100 1-129 20 100 1-26 20 80 2-81 20 80 1-148 20 80 5-123 20 80 5-122 20 80 1-82 20 80 1-209 20 80 2-27 20 80 1-173 20 90 1-273 20 80 1-178 20 80 1-179 20 80 2-32 20 80 1-181 20 80 1-165 20 80 1-351 20 80

TABLE 24c Post-emergence action at 80 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI 3-129 80 80 2-129 80 100 1-129 80 100 6-116 80 90 1-338 80 80 2-338 80 90 2-81 80 90 2-82 80 90 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 80

TABLE 25a Post-emergence action at 5 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 3-129 5 100 2-129 5 80 6-116 5 80 1-26 5 90 2-26 5 80 3-26 5 90 3-208 5 90 1-131 5 90 2-131 5 90 2-149 5 90 5-117 5 80 5-122 5 80 2-87 5 80 1-88 5 80 2-25 5 90 3-27 5 90 1-27 5 80 2-27 5 100 1-273 5 100 2-273 5 80 3-273 5 80 1-44 5 80 2-44 5 80 1-45 5 80 2-31 5 80 1-304 5 90 2-304 5 90 1-305 5 90 2-305 5 80 1-306 5 90 2-306 5 80 2-177 5 90 2-178 5 90 2-179 5 80 2-132 5 80 1-135 5 80 2-135 5 90 1-277 5 90 2-277 5 90 1-278 5 80 2-278 5 90 1-279 5 90 2-195 5 80 2-196 5 80 2-57 5 80 1-58 5 80 2-58 5 80 2-56 5 80 1-57 5 80 2-207 5 80 2-271 5 100 2-32 5 90 2-33 5 90 2-146 5 80 2-73 5 80 1-74 5 80 1-137 5 80 1-183 5 90 2-183 5 80 2-182 5 90 2-181 5 80 2-286 5 90 1-287 5 80 2-287 5 90 2-288 5 80 1-210 5 80 2-213 5 90 1-288 5 90 2-289 5 80 1-291 5 80 2-291 5 80 2-292 5 80 1-271 5 90 2-49 5 80 1-33 5 80 1-32 5 80 1-164 5 80 1-166 5 80 2-272 5 80 1-292 5 80 1-83 5 80 2-83 5 80 2-89 5 90 1-346 5 80 2-345 5 90 2-185 5 80 1-352 5 80 2-350 5 80 2-86 5 80 1-353 5 80

TABLE 25b Post-emergence action at 20 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 3-129 20 100 2-129 20 100 1-129 20 90 6-116 20 90 3-337 20 80 1-26 20 90 2-26 20 90 3-26 20 90 1-208 20 80 2-208 20 80 3-208 20 90 6-159 20 90 1-130 20 80 2-130 20 80 6-117 20 90 1-81 20 80 2-81 20 100 2-82 20 90 1-147 20 100 2-147 20 100 1-148 20 100 2-148 20 90 1-131 20 90 2-131 20 100 6-118 20 80 1-149 20 100 2-149 20 100 6-124 20 80 5-58 20 80 5-117 20 90 5-75 20 80 5-123 20 80 5-122 20 80 1-82 20 80 1-87 20 80 2-87 20 90 1-88 20 80 2-88 20 80 1-25 20 100 2-25 20 100 3-27 20 100 1-27 20 100 2-27 20 100 2-173 20 100 1-273 20 100 2-273 20 90 3-273 20 90 1-44 20 90 2-44 20 80 1-45 20 80 2-45 20 80 1-46 20 80 2-46 20 80 2-31 20 80 1-28 20 80 2-28 20 80 2-29 20 80 1-304 20 90 2-304 20 90 1-305 20 90 2-305 20 90 1-306 20 90 2-306 20 90 1-177 20 90 2-177 20 90 1-178 20 90 2-178 20 90 1-179 20 80 2-179 20 90 1-132 20 80 2-132 20 80 1-135 20 90 2-135 20 90 6-254 20 80 2-134 20 80 2-133 20 90 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 90 1-279 20 90 2-279 20 80 2-195 20 90 2-225 20 80 2-197 20 80 1-226 20 80 2-226 20 80 2-196 20 90 1-56 20 90 2-57 20 90 1-58 20 90 2-58 20 90 2-56 20 90 1-57 20 90 1-207 20 90 2-207 20 90 2-271 20 100 2-32 20 90 2-33 20 90 2-42 20 80 2-146 20 90 5-255 20 80 1-72 20 80 2-72 20 80 1-73 20 80 2-73 20 80 1-74 20 90 2-74 20 80 1-137 20 80 1-136 20 80 2-180 20 80 1-183 20 90 2-183 20 90 2-182 20 90 2-181 20 90 2-228 20 80 2-286 20 90 1-287 20 90 2-287 20 90 2-288 20 90 1-210 20 90 2-210 20 90 2-213 20 100 1-288 20 100 1-289 20 80 2-289 20 90 1-291 20 90 2-291 20 90 2-292 20 90 1-271 20 90 2-47 20 80 1-339 20 80 2-339 20 80 1-49 20 80 2-49 20 80 1-229 20 80 2-229 20 80 1-340 20 80 2-340 20 80 1-33 20 80 1-32 20 90 2-154 20 80 1-155 20 80 2-155 20 90 6-260 20 80 1-164 20 80 2-164 20 80 1-165 20 80 1-166 20 80 2-161 20 80 2-211 20 80 2-272 20 80 2-276 20 90 1-276 20 80 1-274 20 80 1-272 20 90 1-341 20 80 1-292 20 80 2-341 20 80 1-83 20 90 2-83 20 100 1-89 20 80 2-89 20 90 1-345 20 80 2-344 20 80 1-346 20 90 2-345 20 100 1-195 20 80 2-185 20 90 1-84 20 90 2-84 20 80 1-352 20 90 2-350 20 90 1-86 20 80 2-86 20 90 1-92 20 80 2-92 20 80 1-90 20 80 2-90 20 90 1-353 20 90 2-351 20 80 2-352 20 80 2-353 20 80

TABLE 25c Post-emergence action at 80 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 3-338 80 80 6-117 80 90 1-81 80 100 2-81 80 100 2-82 80 90 1-147 80 100 2-147 80 100 1-148 80 100 2-148 80 90

TABLE 26a Post-emergence action at 5 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 1-129 5 80 6-116 5 80 2-26 5 80 3-26 5 80 1-208 5 80 2-208 5 80 3-208 5 80 1-130 5 80 5-59 5 80 5-58 5 80 5-117 5 80 5-75 5 80 1-82 5 80 1-87 5 80 2-87 5 80 1-88 5 80 2-88 5 80 2-25 5 80 3-27 5 90 2-173 5 80 2-44 5 80 1-45 5 80 1-46 5 80 2-31 5 80 2-135 5 80 1-134 5 80 1-277 5 90 2-278 5 80 1-279 5 90 1-227 5 80 2-57 5 80 2-56 5 80 2-32 5 80 1-34 5 90 2-34 5 90 6-255 5 90 2-42 5 90 2-146 5 80 1-138 5 80 1-137 5 80 1-180 5 90 2-182 5 80 1-228 5 80 2-286 5 90 1-287 5 90 2-288 5 80 1-212 5 80 2-213 5 80 1-289 5 80 1-291 5 80 2-291 5 80 2-47 5 80 1-339 5 80 2-339 5 90 1-49 5 80 2-49 5 80 1-47 5 80 2-154 5 90 1-155 5 90 1-164 5 90 1-165 5 90 1-166 5 80 1-159 5 80 2-159 5 80 2-211 5 80 2-272 5 90 2-276 5 80 1-274 5 80 1-292 5 80 1-342 5 80 2-342 5 80 1-345 5 80 1-346 5 80 1-347 5 90 1-195 5 80 1-84 5 90 2-350 5 80 1-86 5 80 2-86 5 80 2-353 5 80

TABLE 26b Post-emergence action at 20 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 3-129 20 90 2-129 20 100 1-129 20 100 6-116 20 80 3-338 20 80 1-26 20 80 2-26 20 80 3-26 20 90 6-26 20 80 1-208 20 90 2-208 20 80 3-208 20 90 6-159 20 80 1-130 20 90 1-147 20 80 1-131 20 90 2-131 20 80 1-149 20 90 2-149 20 90 5-59 20 90 5-58 20 90 5-117 20 90 5-75 20 80 5-74 20 100 5-123 20 80 5-122 20 90 1-82 20 90 1-87 20 90 2-87 20 80 1-88 20 90 2-88 20 90 1-209 20 90 1-25 20 80 2-25 20 90 3-27 20 100 1-27 20 90 2-27 20 90 2-173 20 90 1-273 20 80 3-273 20 80 1-44 20 80 2-44 20 80 1-45 20 80 2-45 20 80 1-46 20 80 2-46 20 80 1-30 20 80 2-30 20 90 1-31 20 80 2-31 20 90 1-28 20 90 2-28 20 80 2-29 20 80 2-304 20 90 1-305 20 90 2-305 20 90 2-306 20 80 1-177 20 80 1-178 20 80 2-178 20 90 2-179 20 80 1-132 20 90 1-135 20 90 2-135 20 80 6-254 20 80 1-134 20 90 2-134 20 90 1-133 20 80 2-133 20 80 6-120 20 90 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 90 1-279 20 90 1-197 20 90 1-227 20 90 1-225 20 80 1-226 20 80 2-226 20 80 1-56 20 80 2-57 20 90 1-58 20 90 2-58 20 90 2-56 20 90 1-57 20 90 1-207 20 80 2-207 20 80 2-32 20 90 1-34 20 90 2-34 20 100 6-255 20 90 2-33 20 90 2-42 20 90 6-256 20 90 2-146 20 90 1-37 20 80 2-143 20 80 1-72 20 80 2-72 20 80 2-73 20 80 1-74 20 90 2-74 20 80 2-144 20 80 1-138 20 90 2-138 20 80 2-141 20 80 1-137 20 80 1-180 20 90 2-180 20 90 1-183 20 80 2-183 20 80 2-182 20 90 6-145 20 80 1-181 20 90 2-181 20 90 1-228 20 80 2-228 20 80 2-286 20 90 1-287 20 100 2-288 20 90 1-210 20 100 2-210 20 90 1-212 20 90 2-213 20 80 1-288 20 80 1-289 20 90 2-289 20 90 6-228 20 80 1-291 20 90 2-291 20 90 6-230 20 80 1-271 20 90 2-47 20 90 2-47 20 90 6-34 20 80 1-339 20 90 2-339 20 90 1-49 20 90 2-49 20 90 1-229 20 80 2-229 20 90 1-340 20 90 6-267 20 80 2-340 20 80 1-47 20 90 1-33 20 80 2-154 20 90 1-155 20 90 2-155 20 80 6-260 20 90 1-164 20 90 1-165 20 90 1-166 20 90 1-156 20 90 2-156 20 90 1-159 20 80 2-159 20 90 1-162 20 80 2-161 20 80 6-266 20 80 2-211 20 80 2-272 20 100 2-276 20 90 1-276 20 90 1-274 20 90 1-272 20 90 1-341 20 80 1-292 20 80 2-341 20 80 1-83 20 90 2-83 20 80 2-89 20 80 6-161 20 80 1-342 20 90 1-343 20 80 2-342 20 90 1-345 20 80 2-344 20 80 1-346 20 90 2-345 20 100 1-347 20 90 2-346 20 80 1-195 20 80 1-184 20 80 2-348 20 80 1-84 20 90 2-84 20 80 1-352 20 90 2-350 20 80 1-86 20 90 2-86 20 90 1-92 20 90 2-92 20 90 1-90 20 90 1-353 20 90 2-351 20 90 2-352 20 80 1-355 20 80 2-353 20 80 1-356 20 80 2-354 20 80

TABLE 26c Post-emergence action at 80 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 90 1-338 80 90 2-338 80 90 3-338 80 90 2-337 80 80 6-117 80 80 1-81 80 80 2-81 80 90 1-147 80 90 2-147 80 80

TABLE 27a Post-emergence action at 5 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 1-72 5 100

TABLE 27b Post-emergence action at 20 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 1-26 20 90 2-26 20 80 6-26 20 80 3-125 20 80 2-130 20 80 1-147 20 90 2-148 20 90 1-149 20 100 2-149 20 80 5-122 20 80 1-88 20 80 1-27 20 90 2-173 20 90 2-30 20 80 1-28 20 80 2-304 20 80 2-305 20 100 1-306 20 80 1-178 20 80 6-141 20 80 1-179 20 80 2-179 20 90 1-207 20 100 1-72 20 100 1-73 20 80 1-74 20 80 2-180 20 100 1-183 20 100 2-287 20 100 1-212 20 100 1-271 20 80

TABLE 27c Post-emergence action at 80 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 3-129 80 90 2-129 80 100 1-129 80 100 6-116 80 80 1-81 80 90 2-81 80 80 2-82 80 80 6-58 80 100 1-147 80 90 2-147 80 80 1-148 80 80 2-148 80 90

TABLE 28a Post-emergence action at 5 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 2-129 5 100 1-129 5 100 6-116 5 100 1-26 5 100 2-26 5 80 1-208 5 80 2-208 5 80 2-131 5 90 1-149 5 100 2-149 5 90 6-124 5 80 5-58 5 80 5-117 5 100 5-253 5 80 5-75 5 80 5-74 5 80 5-123 5 80 5-122 5 80 1-82 5 80 1-87 5 80 2-87 5 80 1-88 5 80 2-88 5 90 1-209 5 100 1-27 5 100 2-27 5 80 1-173 5 90 2-173 5 100 1-273 5 80 2-273 5 80 6-33 5 80 1-28 5 80 1-304 5 90 2-304 5 80 2-305 5 90 1-306 5 90 2-306 5 80 1-177 5 90 2-177 5 90 1-179 5 90 2-179 5 90 1-134 5 90 1-133 5 90 2-133 5 80 1-277 5 90 2-277 5 90 2-278 5 80 1-279 5 90 2-195 5 90 2-197 5 80 1-225 5 90 1-226 5 100 2-226 5 100 1-56 5 100 2-57 5 100 1-58 5 100 2-58 5 90 2-56 5 80 1-57 5 100 1-207 5 100 2-207 5 90 2-271 5 100 6-210 5 90 2-32 5 80 1-34 5 80 2-34 5 80 6-255 5 80 2-33 5 80 1-182 5 90 2-182 5 90 6-145 5 80 2-287 5 80 2-288 5 80 1-210 5 80 1-212 5 80 1-288 5 80 1-289 5 80 1-339 5 80 1-49 5 90 1-229 5 80 1-33 5 80 1-166 5 90 2-272 5 90 1-276 5 80 1-272 5 90 2-158 5 90 1-83 5 80 1-89 5 90 2-89 5 90 1-342 5 90 2-342 5 90 1-344 5 80 2-343 5 90 1-346 5 100 2-345 5 80 1-195 5 100 1-185 5 80 1-349 5 90 2-348 5 80 2-349 5 90 1-84 5 100 2-84 5 80 1-352 5 80 2-86 5 100 1-92 5 90 2-92 5 80 2-352 5 80

TABLE 28b Post-emergence action at 20 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 1-338 20 80 2-338 20 80 6-253 20 90 1-26 20 100 2-26 20 100 6-26 20 80 1-208 20 80 2-208 20 80 1-130 20 80 2-81 20 90 1-131 20 100 2-131 20 100 1-149 20 100 2-149 20 100 6-124 20 90 5-59 20 90 5-58 20 100 5-117 20 100 5-253 20 80 5-75 20 80 5-74 20 90 5-123 20 80 5-122 20 90 1-82 20 90 1-87 20 90 2-87 20 80 1-88 20 90 2-88 20 100 1-209 20 100 1-4 20 80 1-25 20 80 2-25 20 80 3-27 20 90 1-27 20 100 2-27 20 100 1-173 20 90 2-173 20 100 1-273 20 100 2-273 20 90 3-273 20 80 6-212 20 80 4-212 20 80 1-44 20 90 1-45 20 80 2-45 20 80 6-32 20 80 1-46 20 80 6-33 20 80 2-30 20 80 1-28 20 80 1-29 20 80 2-29 20 80 1-304 20 90 2-304 20 80 1-305 20 90 2-305 20 90 1-306 20 90 2-306 20 80 1-177 20 90 2-177 20 90 1-178 20 90 2-178 20 90 1-179 20 90 2-179 20 90 1-132 20 90 2-132 20 80 1-135 20 80 6-254 20 80 1-134 20 90 1-133 20 100 2-133 20 90 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 90 1-279 20 90 2-195 20 100 2-197 20 100 1-225 20 100 1-226 20 100 2-226 20 100 6-165 20 80 6-166 20 100 2-196 20 100 1-56 20 100 6-45 20 100 6-44 20 80 2-57 20 100 6-43 20 90 1-58 20 100 2-58 20 100 2-56 20 100 1-57 20 100 1-207 20 100 2-207 20 100 2-271 20 100 6-210 20 100 2-32 20 100 1-34 20 90 2-34 20 90 6-255 20 90 2-33 20 100 1-72 20 80 2-72 20 80 2-73 20 100 1-74 20 100 2-74 20 90 1-138 20 80 1-137 20 80 1-136 20 80 2-180 20 90 1-182 20 100 2-182 20 100 6-145 20 90 1-181 20 90 2-181 20 90 2-230 20 100 6-169 20 90 2-286 20 80 2-287 20 90 2-288 20 90 1-210 20 90 2-210 20 80 1-212 20 90 1-288 20 100 1-289 20 90 2-289 20 80 1-291 20 80 2-291 20 90 2-292 20 80 1-271 20 80 2-47 20 90 6-34 20 90 1-339 20 90 2-339 20 100 1-49 20 100 2-49 20 90 1-41 20 80 1-229 20 90 2-229 20 80 1-47 20 80 1-33 20 90 6-259 20 90 1-155 20 80 1-165 20 90 1-166 20 90 1-156 20 80 2-156 20 80 6-262 20 80 2-211 20 90 2-272 20 100 2-276 20 80 1-276 20 80 1-274 20 90 1-272 20 90 1-341 20 80 1-292 20 90 2-158 20 90 1-83 20 100 2-83 20 100 1-89 20 90 2-89 20 100 6-76 20 80 6-161 20 90 1-342 20 90 1-343 20 100 2-342 20 90 1-344 20 90 2-343 20 90 1-345 20 90 2-344 20 80 1-346 20 100 2-345 20 100 1-195 20 100 1-185 20 100 2-185 20 80 1-186 20 80 1-349 20 90 1-350 20 80 2-348 20 100 1-351 20 100 2-349 20 100 1-84 20 100 2-84 20 100 1-352 20 100 2-350 20 100 1-86 20 80 2-86 20 100 1-92 20 100 2-92 20 100 1-90 20 90 1-353 20 100 1-354 20 100 2-352 20 80 2-354 20 90

TABLE 28c Post-emergence action at 80 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 100 2-338 80 100 3-338 80 90 6-253 80 100 1-81 80 90 2-81 80 90 2-148 80 80

TABLE 29a Post-emergence action at 5 g/ha against STEME in % Example number Dosage [g/ha] STEME 3-129 5 100 2-129 5 100 1-129 5 100 6-116 5 90 3-338 5 80 1-26 5 90 2-26 5 80 1-208 5 90 2-208 5 80 3-208 5 80 1-130 5 80 2-130 5 80 1-131 5 80 2-131 5 90 1-149 5 90 2-149 5 90 6-124 5 90 5-59 5 90 5-58 5 90 5-117 5 100 5-75 5 90 5-74 5 80 5-123 5 90 5-122 5 90 1-82 5 90 1-87 5 80 2-87 5 80 1-88 5 90 2-88 5 90 1-4 5 80 1-25 5 80 2-25 5 90 1-27 5 100 2-27 5 100 1-173 5 80 2-173 5 100 1-273 5 90 2-273 5 80 3-273 5 80 6-212 5 80 1-44 5 80 2-46 5 80

TABLE 29b Post-emergence action at 20 g/ha against STEME in % Example number Dosage [g/ha] STEME 3-129 20 100 2-129 20 100 1-129 20 100 6-116 20 100 2-338 20 90 3-338 20 100 2-337 20 90 3-337 20 100 1-26 20 90 2-26 20 90 3-26 20 90 6-26 20 80 1-208 20 90 2-208 20 100 3-208 20 90 6-159 20 90 2-125 20 80 3-125 20 80 1-130 20 80 2-130 20 80 6-117 20 90 1-81 20 90 2-81 20 90 2-82 20 80 6-58 20 80 1-147 20 80 2-147 20 80 1-148 20 90 2-148 20 80 1-131 20 100 2-131 20 90 6-118 20 100 1-149 20 90 2-149 20 90 6-124 20 90 5-59 20 100 5-58 20 90 5-117 20 100 5-253 20 80 5-75 20 100 5-74 20 90 5-123 20 90 5-122 20 100 1-82 20 90 1-87 20 100 2-87 20 90 1-88 20 90 2-88 20 100 1-209 20 90 1-4 20 90 1-25 20 100 2-25 20 100 3-27 20 80 1-27 20 100 2-27 20 100 1-173 20 100 2-173 20 100 1-273 20 100 2-273 20 90 3-273 20 90 6-212 20 90 1-44 20 80 2-44 20 80 1-45 20 80 6-32 20 80 1-46 20 80 2-46 20 80 6-33 20 80

TABLE 29c Post-emergence action at 80 g/ha against STEME in % Example number Dosage [g/ha] STEME 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 100 3-338 80 100 6-253 80 90 2-337 80 90 6-117 80 90 1-81 80 90 2-81 80 100 2-82 80 90 6-58 80 80 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 80

TABLE 30a Post-emergence action at 5 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 1-129 5 80 2-337 5 80 1-149 5 80 1-87 5 80 1-88 5 80 1-44 5 80 2-46 5 80 1-304 5 80 1-132 5 90 1-135 5 80 2-133 5 80 1-277 5 80 2-277 5 80 1-278 5 80 1-279 5 80 1-57 5 80 2-207 5 80 2-271 5 80 2-32 5 90 1-72 5 80 1-73 5 80 2-73 5 80 1-74 5 80 1-183 5 80 2-286 5 80 2-287 5 80 1-289 5 80 2-289 5 80 1-271 5 80 1-165 5 80 1-166 5 80 1-341 5 80 1-292 5 80 1-89 5 90 2-89 5 80 1-346 5 80 1-353 5 80

TABLE 30b Post-emergence action at 20 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 2-129 20 80 1-129 20 80 2-338 20 90 3-338 20 90 6-253 20 80 2-337 20 100 3-337 20 90 2-123 20 80 1-26 20 80 1-208 20 80 2-208 20 80 1-81 20 80 2-81 20 80 2-82 20 80 1-147 20 90 2-147 20 80 1-148 20 80 2-148 20 80 1-131 20 90 1-149 20 100 5-59 20 80 5-58 20 80 5-117 20 80 5-122 20 80 1-82 20 80 1-87 20 90 2-87 20 80 1-88 20 90 2-88 20 80 1-209 20 80 1-25 20 80 2-25 20 90 1-27 20 100 2-27 20 80 2-173 20 80 1-273 20 90 3-273 20 80 1-44 20 100 2-44 20 80 1-45 20 80 1-46 20 90 2-46 20 80 1-31 20 80 2-31 20 80 1-304 20 80 2-304 20 90 1-305 20 80 2-305 20 90 1-306 20 90 2-306 20 90 1-177 20 80 2-177 20 80 1-178 20 80 1-179 20 80 1-132 20 90 1-135 20 90 2-135 20 90 6-254 20 80 1-134 20 80 2-134 20 80 1-133 20 90 2-133 20 80 6-120 20 80 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 100 1-279 20 100 2-279 20 90 1-197 20 80 2-227 20 80 1-227 20 80 1-225 20 90 1-226 20 90 2-226 20 90 2-196 20 80 1-56 20 90 2-57 20 90 1-58 20 80 2-56 20 80 1-57 20 90 1-207 20 90 2-207 20 90 2-271 20 90 2-32 20 90 1-34 20 90 2-34 20 80 6-255 20 80 2-42 20 90 2-146 20 80 1-37 20 80 2-37 20 80 1-72 20 90 2-72 20 80 1-73 20 80 2-73 20 90 1-74 20 90 2-74 20 80 1-183 20 90 2-183 20 90 1-181 20 90 1-228 20 90 1-230 20 80 2-230 20 90 2-286 20 80 1-287 20 80 2-287 20 100 2-288 20 80 1-212 20 80 1-289 20 90 2-289 20 100 1-291 20 80 2-291 20 80 2-292 20 80 1-271 20 90 2-47 20 80 1-339 20 90 2-339 20 80 6-258 20 80 1-49 20 90 1-340 20 80 2-340 20 90 1-47 20 80 1-33 20 80 1-32 20 90 1-155 20 80 1-165 20 80 1-166 20 90 1-156 20 80 2-156 20 90 1-276 20 80 1-274 20 80 1-272 20 80 1-341 20 90 1-292 20 90 1-83 20 90 2-83 20 80 1-89 20 90 2-89 20 90 1-342 20 80 1-343 20 80 1-344 20 90 1-345 20 90 2-344 20 80 1-346 20 80 2-345 20 80 1-347 20 90 2-346 20 80 1-195 20 80 1-185 20 80 2-186 20 80 1-349 20 80 1-84 20 90 2-84 20 80 1-352 20 90 2-350 20 80 1-86 20 90 1-92 20 90 2-92 20 90 1-90 20 90 1-353 20 90 2-351 20 90 1-354 20 90 2-352 20 90 1-355 20 90 2-353 20 100 1-356 20 90 2-354 20 90

TABLE 30c Post-emergence action at 80 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 3-129 80 80 2-129 80 90 1-129 80 100 6-116 80 90 1-338 80 100 2-338 80 100 3-338 80 90 6-253 80 90 2-337 80 100 6-117 80 80 1-81  80 90 2-81  80 90 2-82  80 90 1-147 80 90 2-147 80 90 1-148 80 80 2-148 80 90

TABLE 31a Post-emergence action at 5 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 3-129 5 80 2-129 5 80 1-129 5 80 1-26  5 100 1-208 5 80 2-208 5 100 3-208 5 100 1-125 5 100 2-125 5 100 1-130 5 90 2-130 5 90 1-131 5 100 2-131 5 100 1-149 5 100 2-149 5 100 5-58  5 80 5-117 5 90 5-123 5 80 5-122 5 90 2-88  5 80 1-209 5 100 1-25  5 100 2-25  5 80 3-27  5 80 1-27  5 100 2-27  5 100 1-173 5 90 1-273 5 100 1-45  5 80 2-45  5 80 1-46  5 80 2-46  5 80 1-304 5 80 2-304 5 80 6-231 5 90 1-305 5 90 2-305 5 80 2-306 5 90 1-177 5 90 2-177 5 80 1-178 5 80 1-179 5 80 2-179 5 90 1-132 5 80 1-135 5 80 1-134 5 90 2-134 5 80 1-277 5 80 2-277 5 90 1-278 5 90 2-278 5 90 1-279 5 90 2-279 5 80 2-195 5 100 2-225 5 100 2-227 5 90 1-227 5 100 2-197 5 80 1-226 5 100 2-226 5 90 1-56  5 100 2-57  5 90 1-58  5 90 2-58  5 100 2-56  5 80 1-57  5 100 1-207 5 100 2-207 5 100 2-271 5 80 1-146 5 80 1-73  5 80 1-74  5 80 1-183 5 90 2-183 5 100 1-182 5 100 2-287 5 80 2-288 5 90 1-212 5 80 1-288 5 90 1-289 5 80 1-291 5 90 2-291 5 80 2-47  5 80 1-83  5 90 2-83  5 80 1-89  5 90 2-89  5 90 1-345 5 90 2-344 5 90 1-346 5 90 2-345 5 90 1-347 5 80 2-346 5 80 1-195 5 90 2-185 5 100 1-84  5 100 2-84  5 100 1-352 5 100 2-350 5 100 1-86  5 90 2-86  5 100 2-92  5 100 1-90  5 80 2-90  5 100 1-353 5 100 2-351 5 100

TABLE 31b Post-emergence action at 20 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 3-129 20 90 2-129 20 100 1-129 20 100 6-116 20 80 2-338 20 100 3-338 20 90 6-253 20 80 1-337 20 80 3-337 20 100 1-123 20 100 1-26  20 100 2-26  20 80 3-26  20 90 6-26  20 100 1-208 20 100 2-208 20 100 3-208 20 100 1-125 20 100 2-125 20 100 3-125 20 80 1-130 20 90 2-130 20 100 2-82  20 80 1-148 20 80 1-131 20 100 2-131 20 100 6-118 20 80 1-149 20 100 2-149 20 100 6-124 20 100 5-59  20 80 5-58  20 80 5-117 20 100 5-75  20 80 5-123 20 90 5-122 20 90 1-82  20 90 1-87  20 80 2-87  20 100 1-88  20 80 2-88  20 90 1-209 20 100 1-25  20 100 2-25  20 90 3-27  20 100 1-27  20 100 2-27  20 100 1-173 20 90 2-173 20 100 1-273 20 100 1-44  20 80 2-44  20 80 1-45  20 90 2-45  20 100 1-46  20 80 2-46  20 80 1-304 20 90 2-304 20 90 6-231 20 90 1-305 20 90 2-305 20 90 1-306 20 90 2-306 20 90 1-177 20 90 2-177 20 100 1-178 20 80 2-178 20 90 6-141 20 80 1-179 20 90 2-179 20 100 1-132 20 90 2-132 20 90 1-135 20 90 2-135 20 90 1-134 20 90 2-134 20 90 1-133 20 80 2-133 20 80 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 90 1-279 20 90 2-279 20 90 2-195 20 100 2-225 20 100 1-197 20 100 2-227 20 100 1-227 20 100 2-197 20 100 1-225 20 80 1-226 20 100 2-226 20 100 6-165 20 80 1-56  20 100 2-57  20 100 1-58  20 100 2-58  20 100 2-56  20 100 1-57  20 100 1-207 20 100 2-207 20 100 2-271 20 80 6-210 20 80 1-140 20 80 1-146 20 100 1-37  20 80 1-72  20 90 2-72  20 80 6-49  20 80 1-73  20 80 2-73  20 100 6-50  20 80 1-74  20 90 2-74  20 80 1-180 20 90 2-180 20 100 1-183 20 90 2-183 20 100 1-182 20 100 2-182 20 100 1-228 20 80 2-228 20 80 2-286 20 80 1-287 20 80 2-287 20 90 2-288 20 100 1-210 20 90 2-210 20 90 1-212 20 90 2-213 20 90 1-288 20 90 1-289 20 90 2-289 20 90 1-291 20 100 2-291 20 90 2-292 20 80 1-271 20 90 2-47  20 90 2-47  20 80 2-340 20 80 1-47  20 80 1-33  20 80 1-32  20 80 2-155 20 80 1-165 20 80 1-166 20 80 2-156 20 80 2-272 20 80 2-276 20 80 1-276 20 80 1-274 20 80 1-272 20 90 1-341 20 80 1-292 20 80 1-83  20 90 2-83  20 80 1-89  20 90 2-89  20 90 1-342 20 80 1-343 20 80 2-342 20 80 2-343 20 90 1-345 20 100 2-344 20 100 1-346 20 100 2-345 20 90 1-347 20 100 2-346 20 100 1-195 20 100 1-184 20 90 1-185 20 80 2-185 20 100 2-186 20 80 2-348 20 80 1-351 20 80 2-349 20 80 1-84  20 100 2-84  20 100 1-352 20 100 2-350 20 100 1-86  20 100 2-86  20 100 1-92  20 100 2-92  20 100 1-90  20 100 2-90  20 100 1-353 20 100 2-351 20 100 1-354 20 90 2-352 20 90 1-355 20 100 2-353 20 80 1-356 20 90 2-354 20 100

TABLE 31c Post-emergence action at 80 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 3-129 80 100 2-129 80 100 1-129 80 100 6-116 80 100 1-338 80 90 2-338 80 100 3-338 80 100 6-253 80 80 2-337 80 90 6-117 80 80 1-81  80 80 2-81  80 90 2-82  80 80 1-147 80 80 2-147 80 80 1-148 80 90 2-148 80 80

TABLE 32a Post-emergence action at 5 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 1-26  5 90 2-26  5 90 6-26  5 90 1-208 5 80 2-208 5 80 6-159 5 80 1-130 5 90 2-130 5 80 1-131 5 100 2-131 5 90 6-118 5 100 1-149 5 100 2-149 5 100 5-59  5 90 5-58  5 90 5-117 5 90 5-75  5 90 5-74  5 90 5-123 5 90 5-122 5 90 1-82  5 90 1-87  5 100 2-87  5 90 1-88  5 90 2-88  5 90 1-4  5 80 1-25  5 90 2-25  5 80 1-27  5 90 2-27  5 100 1-173 5 90 1-273 5 90 2-273 5 80 3-273 5 80 6-212 5 80 1-44  5 80 1-45  5 80 6-32  5 80 1-46  5 80 2-305 5 80 1-306 5 90 2-306 5 80 1-177 5 90 1-179 5 90 6-254 5 80 1-133 5 90 1-277 5 90 2-277 5 90 1-278 5 90 2-278 5 90 1-279 5 90 2-279 5 90 2-195 5 80 1-197 5 100 1-227 5 100 1-225 5 90 1-226 5 90 1-56  5 90 6-45  5 90 6-44  5 80 2-57  5 90 6-43  5 90 1-58  5 100 2-58  5 100 2-56  5 90 1-57  5 100 1-207 5 90 2-207 5 80 6-210 5 90 1-34  5 80 2-34  5 80 6-255 5 90 6-256 5 80 1-181 5 90 1-228 5 90 2-228 5 80 2-286 5 90 1-287 5 100 2-287 5 90 2-288 5 90 1-210 5 80 2-210 5 80 1-212 5 90 1-288 5 90 1-289 5 90 2-289 5 90 1-291 5 90 2-291 5 90 2-292 5 90 1-271 5 90 2-47  5 90 1-339 5 90 2-339 5 80 1-49  5 80 2-49  5 90 1-41  5 80 1-229 5 90 2-340 5 80 1-155 5 90 6-260 5 90 1-165 5 90 1-166 5 90 2-272 5 90

TABLE 32b Post-emergence action at 20 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 1-26  20 100 2-26  20 90 6-26  20 90 1-208 20 90 2-208 20 90 6-159 20 90 1-130 20 90 2-130 20 80 6-117 20 80 1-81  20 80 2-81  20 90 2-82  20 90 6-58  20 80 1-147 20 90 2-147 20 90 1-148 20 90 2-148 20 90 1-131 20 100 2-131 20 90 6-118 20 100 1-149 20 100 2-149 20 100 6-124 20 90 5-59  20 90 5-58  20 100 5-117 20 90 5-253 20 80 5-75  20 90 5-74  20 90 5-123 20 90 5-122 20 90 1-82  20 90 1-87  20 100 2-87  20 90 1-88  20 90 2-88  20 90 6-75  20 90 1-209 20 90 1-4  20 90 1-25  20 100 2-25  20 90 3-27  20 100 1-27  20 100 2-27  20 100 1-173 20 100 2-173 20 80 1-273 20 90 2-273 20 90 3-273 20 90 6-212 20 90 1-44  20 90 1-45  20 80 2-45  20 80 6-32  20 80 1-46  20 80 2-31  20 80 2-28  20 80 1-304 20 90 1-305 20 80 2-305 20 90 1-306 20 90 2-306 20 90 1-177 20 90 6-141 20 80 1-179 20 90 1-132 20 90 2-132 20 80 1-135 20 90 2-135 20 80 6-254 20 90 1-134 20 90 2-134 20 80 1-133 20 90 1-277 20 90 2-277 20 90 1-278 20 90 2-278 20 90 1-279 20 90 2-279 20 90 2-195 20 90 2-225 20 100 1-197 20 100 2-227 20 100 1-227 20 100 2-197 20 90 1-225 20 90 1-226 20 100 2-226 20 80 6-165 20 90 2-196 20 90 1-56  20 100 6-45  20 90 6-44  20 90 2-57  20 100 6-43  20 100 1-58  20 100 2-58  20 100 2-56  20 100 1-57  20 100 1-207 20 100 2-207 20 100 6-210 20 90 2-32  20 90 1-34  20 90 2-34  20 100 6-255 20 100 6-256 20 90 1-181 20 90 1-228 20 90 2-228 20 80 1-230 20 90 2-230 20 90 2-286 20 90 1-287 20 100 2-287 20 90 2-288 20 90 1-210 20 90 2-210 20 90 1-212 20 100 2-212 20 100 2-213 20 90 1-288 20 100 1-289 20 90 2-289 20 100 6-228 20 80 1-291 20 100 2-291 20 100 2-292 20 90 1-271 20 100 2-47  20 90 6-34  20 80 1-339 20 90 2-339 20 90 6-258 20 90 1-49  20 90 2-49  20 90 1-41  20 90 1-229 20 90 1-340 20 90 2-340 20 90 1-47  20 90 1-33  20 90 2-154 20 90 6-259 20 90 1-155 20 90 6-260 20 90 1-164 20 80 6-261 20 90 1-165 20 90 1-166 20 90 1-156 20 90 2-156 20 80 6-262 20 90 6-264 20 80 2-211 20 80 2-272 20 90

TABLE 32c Post-emergence action at 80 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 2-337 80 90 6-117 80 90 1-81  80 90 2-81  80 90 2-82  80 90 6-58  80 90 1-147 80 90 2-147 80 90 1-148 80 90 2-148 80 90

Comparative Experiments

In the experiments that follow, herbicidal action of numerous inventive compounds and the structurally closest compounds known from D1 (WO 2012/028579 A1) were compared under the above-specified conditions by the pre-emergence and post-emergence method. The example numbers given in the tables relate to the compounds disclosed in the respective documents.

TABLE 5 Herbicidal pre-emergence action Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA ABUTH MATIN STEME VIOTR 1-129, inventive 80 100 100 100 100 100 100 4-251, from Di 80 0 0 50 70 70 0 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA SETVI AMARE STEME VIOTR 1-147, inventive 80 90 100 100 100 100 100 4-251, from DI 80 0 0 20 70 70 0 Dosage Herbicidal action against Example No.: (g a.i./ha) ALOMY AVEFA SETVI STEME HORMU 2-147, inventive 80 90 100 100 70 90 5-251, from DI 80 0 0 80 40 10 Dosage Herbicidal action against Example No.: (g a.i./ha) AVEFA MATIN ABUTH AMARE STEME VIOTR 1-129, inventive 20 100 100 100 100 100 100 4-251, from DI 20 0 0 40 0 30 80 Dosage Herbicidal action against Example No.: (g a.i./ha) AVEFA SETVI ABUTH MATIN POLCO VIOTR 2-129, inventive 20 100 100 100 100 100 100 5-251, from Di 20 0 30 70 70 40 80

TABLE 6 Herbicidal post-emergence action Example Dosage Herbicidal action against No.: (g a.i./ha) ALOMY AVEFA MATIN PHBPU POLCO VIOTR 1-147, 20 80 90 100 80 90 70 inventive 4-251, 20 20 0 30 60 30 50 from Di Example Dosage Herbicidal action against No.: (g a.i./ha) ALOMY AVEFA LOLRI MATIN PHBPU HORMU 2-147, 20 80 90 70 100 70 80 inventive 5-251, 20 60 30 30 50 50 30 from DI Example Dosage Herbicidal action against No.: (g a.i./ha) ALOMY ECHCG SETVI ABUTH STEME VIOTR 1-129, 5 90 100 100 100 100 80 inventive 4-251, 5 0 50 0 70 60 20 from DI Example Dosage Herbicidal action against No.: (g a.i./ha) ALOMY AVEFA SETVI AMARE MATIN HORMU 2-129, 5 100 100 100 100 80 80 inventive 5-251, 5 30 20 30 80 30 20 from DI 

1. An isophthalamide of formula (I) or salt thereof

in which the symbols and indices are defined as follows: Q is Q¹, Q², Q³ or Q⁴

R¹ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, R² is (C₁-C₆)-alkyl, R^(x) is (C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl or phenyl, R^(y) is halogen, (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl, R^(z) is hydrogen, (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl, X is halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O, R²(O)_(n)S or R¹O—(C₁-C₆)-alkyl or R²S(O)_(n)-(C₁-C₆)-alkyl, Y is halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O or R(O)_(n)S, Z is hydrogen, one of the following groups, each of which is substituted by s radicals from the group consisting of halogen, cyano, R¹C(O), R¹OC(O), R¹O and R²(O)_(n)S: (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyl-(C₁-C₆)-alkyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, R²S(O)n-(C₁-C₆)-alkyl, R¹C(O), R¹OC(O), R¹C(O)—(C₁-C₆)-alkyl, R¹OC(O)—(C₁-C₆)-alkyl, R¹NH—(C₁-C₆)-alkyl, R¹ ₂N—(C₁-C₆)-alkyl, R¹NHC(O)—(C₁-C₆)-alkyl or R¹ ₂NC(O)—(C₁-C₆)-alkyl, or one of the following groups, each substituted by s radicals from the group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, R¹C(O) and R¹OC(O): phenyl, benzyl, phenyl, benzyl, heterocyclyl or heterocyclyl-(C₁-C₆)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 2. The isophthalamide as claimed in claim 1, wherein Q is Q¹, Q², Q³ or Q⁴

R^(x) is Me, Et, Pr, i-Pr, c-Pr, (CH₂)₂OMe or Ph, R^(y) is Cl, Me, Et or CF₃, R^(z) is hydrogen, Me, Et or CF₃, X is halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, c-Pr, OMe, OEt, SMe, SEt, SO₂Me, SO₂Et, CH₂OMe, CH₂SMe, CH₂SO₂Me, (CH₂)₂SMe or (CH₂)₂SO₂Me, Y is halogen, halo-(C₁-C₆)-alkyl, OMe, SMe, S(O)Me, SO₂Me, SEt, S(O)Et or SO₂Et, Z is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, CH₂c-Pr, halo-(C₁-C₆)-alkyl, (CH₂)₂OMe, (CH₂)₂OEt, allyl, propynyl, (CH₂)₂SMe, (CH₂)₂SO₂Me, C(O)Me, C(O)cPr, C(O)OMe, C(O)OEt, CH₂-(tetrahydrofuran-2-yl), oxetan-3-yl, CH₂C(O)Me, CH₂C(O)c-Pr, CH₂C(O)NMe₂, CH₂CN, Ph, CH₂Ph or CH₂-(thien-2-yl), OMe, OEt, OPr, Oi-Pr.
 3. The isophthalamide as claimed in claim 1, wherein Q is Q¹ or Q⁴, R^(x) is Me, Et or Pr, R^(z) is H or Me, X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt, CH₂OMe or CF₃, Y is F, Cl, Br, I, SMe, S(O)Me, SO₂Me, CF₃, CHF₂ or C₂F₅, Z is hydrogen, Me, Et, c-Pr, Pr, i-Pr, c-Bu, CH₂-c-Pr, CH₂CHF₂, CH₂CF₃, CH(Me)-c-Pr, (CH₂)₂OMe, (CH₂)₂SMe, CH₂CN, CH₂-(tetrahydrofuran-2-yl), CH₂C(O)NMe₂, Ph or CH₂-(thien-2-yl), oxetan-3-yl, OMe, OEt, OPr, Oi-Pr.
 4. An herbicidal composition or plant growth-regulating composition, comprising one or more isophthalamides of formula (I) or salts thereof as claimed in claim
 1. 5. The herbicidal composition as claimed in claim 4, further comprising a formulation auxiliary.
 6. The herbicidal composition as claimed in claim 4, comprising at least one further active ingredient from the group of insecticides, acaricides, herbicides, fungicides, safeners and/or growth regulators.
 7. The herbicidal composition as claimed in claim 4, comprising a safener.
 8. The herbicidal composition as claimed in claim 7, in which the safener is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor and dichlormid.
 9. A method of controlling one or more unwanted plants, comprising applying an effective amount of at least one isophthalamide of formula (I) and/or salt thereof as claimed in claim 1 or an herbicidal composition thereof to the plants and/or to a site of unwanted vegetation.
 10. A product comprising one or more compounds of formula (I) and/or salts as claimed in claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.
 11. The product as claimed in claim 10, wherein the isophthalamides of formula (I) and/or salts are used for controlling one or more unwanted plants in one or more crops of one or more useful plants.
 12. The product as claimed in claim 11, wherein the useful plants are transgenic useful plants. 